1H-pyrrolo(2,3-b)pyridin-5-amine → N-[1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

HRID 1020374Notes

Reaction equation

HRID 1020374 reaction equation
OC1(C2C=CC=CC=2)[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:19][C:18]=3[C:28]([F:31])([F:30])[F:29])=[O:16])=[CH:10][CH:9]=2)CC1.N[C:39]1C=C2C(=NC=1)NC=C2>>[NH:5]1[C:8]2=[N:13][CH:12]=[C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH2:25][CH:24]([CH3:39])[CH2:23]4)=[N:19][C:18]=3[C:28]([F:30])([F:31])[F:29])=[O:16])[CH:10]=[C:9]2[CH:7]=[CH:6]1

Participants

3

Reactant 2

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 46208786N-[6-(4-hydroxy-4-phenylpiperidin-1-yl)pyridin-3-yl]-2-(piperidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxamide

Product 1

HCID 67390591N-[1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(3-methyl-1-piperidinyl)-4-(trifluoromethyl)-5-oxazolecarboxamide

Procedure

Compound 54 was prepared by the general procedure for compound 1, by using compound A-10 and 5-amino-7-azaindole as starting materials. 1H NMR (500 MHz, DMSO-d6) δ 11.67 (s, 1H), 10.21 (s, 1H), 8.37 (s, 1H), 8.23 (s, 1H), 7.50 (s, 1H), 6.46 (m, 1H), 4.13 (m, 2H), 3.07 (m, 1H), 2.75 (t, 1H, J=11.7 Hz), 1.77 (m, 2H), 1.67 (m, 1H), 1.54 (m, 1H), 1.15 (m, 1H), 0.94 (d, 3H, J=6.3 Hz). MS (M+1): 394.

Sources & evidence

ORD record
ord-31ba2becf0c64efa97cd706d64f7b19e
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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