Diisopropylethylamine → HCID 69421103, compound

HRID 1375079Notes

Reaction equation

HRID 1375079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:57]([O:61][C:62](=[O:76])[CH2:63][C:64]1([C:69]2[CH:74]=[CH:73][C:72]([NH2:75])=[CH:71][CH:70]=2)[CH2:68][CH2:67][CH2:66][CH2:65]1)([CH3:60])([CH3:59])[CH3:58]>CN(C)C=O.CO.ClCCl>[C:57]([O:61][C:62](=[O:76])[CH2:63][C:64]1([C:69]2[CH:74]=[CH:73][C:72]([NH:75][C:21](=[O:23])[CH2:20][C:5]3[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:71][CH:70]=2)[CH2:68][CH2:67][CH2:66][CH2:65]1)([CH3:60])([CH3:58])[CH3:59]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 69419644HCID 69419644, compound

Product 1

HCID 69421103HCID 69421103, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of [3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid (0.26 g, prepared as described in Example 52 of International Patent Application Publication No. WO 96/22966) in dry dimethylformamide (15 mL), under argon, was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.32 g). This solution was stirred at room temperature for 10 minutes and then treated with diisopropylethylamine (0.28 ml) and a solution of [1-(4-amino-phenyl)-cyclopentyl]-acetic acid tert-butyl ester (0.21 g, Reference Example 5a) in dry dimethylformamide (5 mL). The resulting amber coloured solution was stirred at room temperature for 2 hours and then evaporated to low bulk. The residue was partitioned between water (containing 1 mL of 1M hydrochloric acid solution) and ethyl acetate. The organic phase was washed with water, then with brine, then dried over magnesium sulfate and then evaporated to yield a fawn solid which was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (49:1, v/v) to give the title compound (0.30 g) as a pale yellow solid. MS(ES+): 594(M+Na)+; MS (ES−): 570 (M−H).

Workup

  1. stirringwas stirred at room temperature for 2 hours
  2. customevaporated to low bulk
  3. customThe residue was partitioned between water (containing 1 mL of 1M hydrochloric acid solution) and ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialwith brine, then dried over magnesium sulfate
  6. customevaporated
  7. customto yield a fawn solid which

Sources & evidence

ORD record
ord-3ffbfa52654b4eb7b4b98f302de0e1d7
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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