2-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide → HCID 67356402, compound

HRID 627430Notes

Reaction equation

HRID 627430 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[N:8]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:6]=2[N:7]=1.[CH2:21]1[N:26]([C:27]2[CH:28]=[CH:29][C:30]([NH2:33])=[N:31][CH:32]=2)[CH2:25][CH2:24][N:23]2[CH2:34][CH2:35][CH2:36][CH:22]12>>[CH:16]1([N:8]2[C:6]3[N:7]=[C:2]([NH:33][C:30]4[CH:29]=[CH:28][C:27]([N:26]5[CH2:25][CH2:24][N:23]6[CH2:34][CH2:35][CH2:36][CH:22]6[CH2:21]5)=[CH:32][N:31]=4)[N:3]=[CH:4][C:5]=3[CH:10]=[C:9]2[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamideHCID 67355217HCID 67355217, compound

Product 1

HCID 67356402HCID 67356402, compoundYield 37.2%

Procedure

Following general N—C coupling procedure 1, 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (100 mg, 0.34 mmole) was combined with 5-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)pyridin-2-amine (74.6 mg, 0.34 mmole) which gave 7-cyclopentyl-2-(5-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (60 mg) in 37% yield. 1H NMR (400 MHz, DMSO) δ 9.30 (s, 1H). 8.77 (s, 1H), 8.18-8.12 (m, 1H), 8.02-7.98 (m, 1H), 7.48-7.40 (m, 1H), 6.59 (s, 1H), 4.78-4.68 (m, 1H), 3.77-3.72 (m, 1H), 3.62-3.55 (m, 1H), 3.08 (s, 3H), 3.04 (s, 3H), 2.77-2.63 (m, 2H), 2.51-2.31 (m, 4H), 2.30-2.21 (m, 1H), 2.13-1.91 (m, 6H), 1.88-1.58 (m, 5H), 1.43-1.33 (m, 1H) HR-MS m/z 475.2941 (M+H)+

Sources & evidence

ORD record
ord-6ff12380dd4b4927967e1cfcfc57f1d0
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

Loading…