1-(3,8-Diazabicyclo[3.2.1]octan-8-yl)ethan-1-one → HCID 67355577, compound

HRID 1850543Notes

Reaction equation

HRID 1850543 reaction equation
[CH:1]1([N:8]2[C:12]3[N:13]=[C:14]([NH:17][C:18]4[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][N:19]=4)[N:15]=[CH:16][C:11]=3[CH:10]=[C:9]2[C:27](=[O:31])[N:28]([CH3:30])[CH3:29])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:32]12[N:39]([C:40](=[O:42])[CH3:41])[CH:36]([CH2:37][CH2:38]1)[CH2:35][NH:34][CH2:33]2>>[C:40]([N:39]1[CH:36]2[CH2:37][CH2:38][CH:32]1[CH2:33][N:34]([C:22]([C:21]1[CH:25]=[CH:26][C:18]([NH:17][C:14]3[N:15]=[CH:16][C:11]4[CH:10]=[C:9]([C:27]([N:28]([CH3:29])[CH3:30])=[O:31])[N:8]([CH:1]5[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:12]=4[N:13]=3)=[N:19][CH:20]=1)=[O:23])[CH2:35]2)(=[O:42])[CH3:41]

Participants

3

Reactant 2

HCID 124306021-(3,8-Diazabicyclo[3.2.1]octan-8-yl)ethan-1-oneHCID 673554046-(7-Cycloheptyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid

Product 1

HCID 67355577HCID 67355577, compoundYield 88%

Procedure

Following general amide formation method 3, 6-(7-cycloheptyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with 1-(3,8-diazabicyclo[3.2.1]octan-8-yl)ethanone which gave 2-(5-(8-acetyl-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-7-cycloheptyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (63 mg) in 88% yield. 1H NMR (400 MHz, CDCl3) δ ppm 9.69 (s, 1H) 8.90 (s, 1H) 8.72 (d, J=8.59 Hz, 1H) 8.51 (d, J=2.02 Hz, 1H) 7.78 (dd, J=8.84, 2.27 Hz, 1H) 6.46 (s, 1H) 4.71 (br. s., 1H) 4.51 (tt, J=11.12, 4.04 Hz, 1H) 4.16 (br. s., 1H) 3.24-3.10 (m, 7H) 2.70-2.55 (m, 2H) 2.18-2.06 (m, 4H) 2.01 (ddd, J=13.64, 7.07, 4.04 Hz, 4H) 1.95-1.79 (m, 5H) 1.79-1.62 (m, 5H) 1.62-1.49 (m, 2H). HR-MS (m/z MH+) 559.31 RT 3.89 min.

Sources & evidence

ORD record
ord-79247495aedc4dc2b9eef6dfd5ef0ec4
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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