Benzenepropanoic acid → HCID 66761187, compound

HRID 389570Notes

Reaction equation

HRID 389570 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[N:16][C:15]([NH2:18])=[C:14]4[O:19][C:20]([C:22]5[C:30]6[C:25](=[CH:26][N:27]=[CH:28][CH:29]=6)[S:24][CH:23]=5)=[CH:21][C:13]=34)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[C:40](O)(=[O:49])[CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[NH2:18][C:15]1[N:16]=[CH:17][C:12]([C:10]2[CH:9]=[N:8][N:7]([CH:4]3[CH2:3][CH2:2][N:1]([C:40](=[O:49])[CH2:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH2:6][CH2:5]3)[CH:11]=2)=[C:13]2[CH:21]=[C:20]([C:22]3[C:30]4[C:25](=[CH:26][N:27]=[CH:28][CH:29]=4)[S:24][CH:23]=3)[O:19][C:14]=12

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66760792HCID 66760792, compound

Product 1

HCID 66761187HCID 66761187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1-piperidin-4-yl-1H-pyrazol-4-yl)-2-thieno[2,3-c]pyridin-3-yl-furo[2,3-c]pyridin-7-ylamine (20.8 mg, 0.05 mmol) in DMF (0.5 mL) was added diisopropylethylamine (0.05 mL, 6.5 mmol), dihydrocinnamic acid (0.06 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodimide hydrochloride (13.5 mg, 0.07 mmol). The resulting solution was allowed to stir at room temperature overnight. The mixture was concentrated and then purified by MDP to afford the title compound. 1H NMR (400 MHz, CD3OD): δ 9.50 (s, 1H), 9.10 (s, 1H), 8.59 (d, J=6.1 Hz, 1H), 8.72 (d, J=6.1 Hz, 1H), 8.28 (s, 1H), 8.05 (s, 1H), 7.88 (s, 1H), 7.87 (s, 1H), 7.28 (s, 5H), 4.54 (m, 1H), 4.04 (m, 2H), 3.10 (m, 2H), 2.99 (m, 2H), 2.67 (m, 2H), 2.19 (m, 2H), 1.95 (m, 2H); MS (ESI): 549.64 [M+H]+; HPLC tR=0.86 min (HPLC: Analytical—2 min).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by MDP

Sources & evidence

ORD record
ord-c9ef68f984354161a0e5891289838f3c
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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