Diisopropylethylamine → HCID 178484656, compound

HRID 80702

Reaction equation

HRID 80702 reaction equation
[NH2:1][C:2]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][N:4]1[C:11](=[O:29])[C:12]([OH:28])=[C:13]([C:15]3[NH:16][CH:17]=[C:18]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[N:19]=3)[N:14]=[C:3]21.[CH3:30][N:31]([CH3:37])[C:32](=[O:36])[C:33](O)=[O:34].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C:18]2[N:19]=[C:15]([C:13]3[N:14]=[C:3]4[C:2]5([NH:1][C:33](=[O:34])[C:32]([N:31]([CH3:37])[CH3:30])=[O:36])[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]5)[CH2:5][N:4]4[C:11](=[O:29])[C:12]=3[OH:28])[NH:16][CH:17]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2760995N,N-Dimethyloxamic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178507110HCID 178507110, compound2×

Product 1

HCID 178484656HCID 178484656, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10-amino-2-(4-(4-fluorobenzyl)-1H-imidazol-2-yl)-3-hydroxy-7,8,9,10-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-4(6H)-one, Example 1 (27 mg, 0.068 mmol) and 2-(dimethylamino)-2-oxoacetic acid (11.99 mg, 0.102 mmol) in DMF (3 mL) was added N,N-diisopropylethylamine (0.061 mL, 0.35 mmol), DMAP (1.668 mg, 0.014 mmol) and HATU (38.9 mg, 0.102 mmol) and the resulting mixture stirred at room temp for 3 h. The mixture was then concentrated and purified by preparative HPLC to afford the title compound (6 mg, 8% yield) as an off-white solid. 1H NMR (500 MHz, CDCl3) δ ppm 1.63-1.77 (m, 2H), 1.93-1.98 (m, 2H), 2.29-2.38 (m, 4H), 2.50 (br. s., 1H), 3.00 (s, 3H), 3.17 (s, 3H), 4.03 (s, 2H), 4.14 (s, 2H), 6.82 (br. s., 1H), 7.00 (t, J=8.39 Hz, 1H), 7.21-7.27 (m, 3H), 7.70 (s, 1H). LCMS (M+H)=495.20.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-60e03a355343462ea83dbec07e7a8184
Source dataset
uspto-grants-2014_09
Patent number
US08846659B2

Linked notes

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