HCID 67355362, compound → HCID 67379489, compound

HRID 1850594Notes

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[CH2:21][CH2:20][CH2:19][O:18][CH2:17]3)[C:6]=2[N:7]=1.[NH2:22][C:23]1[CH:45]=[CH:44][C:26]([C:27]([N:29]2[CH2:35][CH:34]3[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:28])=[CH:25][N:24]=1>>[CH3:14][N:13]([CH3:15])[C:11]([C:9]1[N:8]([CH:16]2[CH2:21][CH2:20][CH2:19][O:18][CH2:17]2)[C:6]2[N:7]=[C:2]([NH:22][C:23]3[CH:45]=[CH:44][C:26]([C:27]([N:29]4[CH2:30][CH:31]5[N:36]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])[CH:34]([CH2:33][CH2:32]5)[CH2:35]4)=[O:28])=[CH:25][N:24]=3)[N:3]=[CH:4][C:5]=2[CH:10]=1)=[O:12]

Participants

Reactant 2

HCID 67355362HCID 67355362, compound

HCID 86686646HCID 86686646, compound

Product 1

HCID 67379489HCID 67379489, compoundYield 25.4%

Procedure

Following general N—C coupling procedure 1, 2-chloro-N,N-dimethyl-7-(tetrahydro-2H-pyran-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (80 mg, 0.26 mmole) was combined with tert-butyl 3-(6-aminonicotinoyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (82 mg, 0.26 mmole) which gave tert-butyl 3-(6-(6-(dimethylcarbamoyl)-7-(tetrahydro-2H-pyran-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinoyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (40 mg) in 25% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.84 (s, 1H), 8.72-8.65 (m, 1H), 8.42 (m, 1H), 7.89-7.82 (m, 1H), 6.56 (s, 1H), 4.63-4.52 (m, 1H), 4.52-4.41 (m, 1H), 4.26 (br, 2H), 4.08-3.96 (m, 2H), 3.70-3.49 (m, 3H), 3.16 (S, 6H), 3.23-3.02 (m, 1H), 3.03-2.88 (m, 1H), 2.18-2.07 (m, 1H), 2.02-1.57 (m, 7H), 1.51 (s, 9H). HR-MS m/z 605.3201 (M+H)+

Sources & evidence

ORD record: ord-2aafa06a2bbe4a4abb54e1cc1e3fd519
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957074B2

Reaction notes

Loading…