3-{2-[(cyclopropylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one → 3-{2-[(cyclohexylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 633543Notes

Reaction equation

HRID 633543 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[C:19]2[C:27]3[C:22](=[C:23]([O:28]C)[N:24]=[CH:25][CH:26]=3)[N:21]([CH3:30])[CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(CNC2C=CC(S(C)(=O)=O)=CC=2C2C3C=CNC(=O)C=3N(C)C=2)CC1>>[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[C:19]2[C:27]3[CH:26]=[CH:25][NH:24][C:23](=[O:28])[C:22]=3[N:21]([CH3:30])[CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 903883093-{2-[(cyclopropylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-oneHCID 90416399N-(cyclohexylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)aniline

Product 1

HCID 862878913-{2-[(cyclohexylmethyl)amino]-5-(methylsulfonyl)phenyl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Procedure

The title compound was prepared according to the procedure in Example 44C substituting the product from Example 47A for the product from Example 44C (0.027 g, 53%). 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 7.64 (dd, J=8.70, 2.29 Hz, 1H) 7.44-7.46 (m, 2H) 6.93 (d, J=7.02 Hz, 1H) 6.83 (d, J=8.85 Hz, 1H) 6.24 (d, J=6.71 Hz, 1H) 4.12 (s, 3H) 3.09 (s, 3H) 3.06 (d, J=7.32 Hz, 2H) 2.10-2.17 (m, 1H) 1.61-1.69 (m, 2H) 1.51-1.58 (m, 2H) 1.44-1.50 (m, 4H) 1.15-1.24 (m, 2H). MS (ESI+) m/z 414 (M+H)+.

Sources & evidence

ORD record
ord-7a928c0ba3c14f4da967465a23ef7e44
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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