Methyl 4-aminobenzoate → HCID 86701936, compound

HRID 715763Notes

Reaction equation

HRID 715763 reaction equation
C1([CH2:6][C:7](Cl)=[O:8])CCCC1.[N:10]1[CH:11]=[CH:12][N:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][C:21]([C:23]3[S:24][C:25]([C:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=4)=[CH:26][CH:27]=3)=[O:22])=[CH:15][C:14]=12.NC1C=CC(C(OC)=O)=CC=1>>[C:7]([N:31]1[CH2:30][CH:29]=[C:28]([C:25]2[S:24][C:23]([C:21]([NH:20][CH2:19][C:16]3[CH:17]=[CH:18][N:13]4[CH:12]=[CH:11][N:10]=[C:14]4[CH:15]=3)=[O:22])=[CH:27][CH:26]=2)[CH2:33][CH2:32]1)(=[O:8])[CH3:6]

Participants

4

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 3485182Cyclopentylacetyl chlorideHCID 86701937HCID 86701937, compound

Product 1

HCID 86701936HCID 86701936, compound

Procedure

The title compound was prepared as described in Example 52A, substituting acetyl chloride for 2-cyclopentylacetyl chloride and N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-(1,2,3,6-tetrahydropyridin-4-yl)thiophene-2-carboxamide for methyl 4-aminobenzoate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.13-9.06 (m, 1H), 8.48 (d, J=7.0 Hz, 1H), 7.88 (s, 1H), 7.72 (d, J=3.9 Hz, 1H), 7.51 (d, J=1.2 Hz, 1H), 7.38 (s, 1H), 7.15 (t, J=4.2 Hz, 1H), 6.83 (dd, J=7.0, 1.6 Hz, 1H), 6.28-6.21 (m, 1H), 4.46 (d, J=5.9 Hz, 2H), 4.15-4.04 (m, 2H), 3.61 (dt, J=11.3, 5.6 Hz, 2H), 2.63-2.35 (m, 2H), 2.07-1.99 (m, 3H); MS (ESI)(+)) m/e 381 (M+H)+.

Sources & evidence

ORD record
ord-b06151ee62e84366842c6821358ad501
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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