Isopropylamine → HCID 57665467, compound

HRID 1173034Notes

Reaction equation

HRID 1173034 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:5][C:6]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18]([OH:20])=O)=[CH:11][CH:10]=1.CN(C(ON1N=[N:46][C:41]2[CH:42]=CC=N[C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>ClCCl.CN(C=O)C>[CH:41]([NH:46][C:18]([CH:16]1[CH2:17][CH:15]1[C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][C:6]2[S:5][C:4]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=3)=[N:3][C:2]=2[CH3:1])=[CH:10][CH:11]=1)=[O:20])([CH3:42])[CH3:40]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11487291(+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

Product 1

HCID 57665467HCID 57665467, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (+)-(trans)-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (III-3c) (0.12 g, 0.28 mmol) in dichloromethane (2 mL) and DMF (1 mL) was added HATU (0.16 g, 0.42 mmol). The mixture was stirred for 15 min followed by addition of isopropylamine (0.02 g, 0.33 mmol). The solution stirred for 6 h after which the dichloromethane was removed via rotavap. Sat. NaHCO3 and ethyl acetate were added and the organic layer separated and washed with H2O, dried over MgSO4, filtered and concentrated. The resulting oil was triterated with Et2O and formed a yellow ppt which was filtered and dried under high vacuum to give the title compound as a yellow powder (0.08 g, 61%). 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 6.95 (d, J=8.4 Hz, 2H), 6.59 (d, J=8.4 Hz, 2H), 5.49 (d, J=7.9 Hz, 1H), 4.44 (s, 2H), 4.13-4.08 (m, 1H), 2.49 (s, 3H), 2.40-2.37 (m, 1H), 1.56-1.51 (m, 1H), 1.44-1.39 (m, 1H), 1.26-1.10 (m, 7H). ES-MS m/z 474.2 (MH+).

Workup

  1. customwas removed via rotavap
  2. additionSat. NaHCO3 and ethyl acetate were added
  3. customthe organic layer separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customformed a yellow ppt which
  9. filtrationwas filtered
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-8e63f898aad441c3906657f3f14c82e1
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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