Formaldehyde → HCID 67356062, compound

HRID 1850660Notes

Reaction equation

HRID 1850660 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[C:27](=[O:28])[CH2:26][C@@H:25]5[NH:29][C@@H:22]([CH2:23][CH2:24]5)[CH2:21]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[CH2:37]=O>>[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[N:30]([CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[C:27](=[O:28])[CH2:26][C@@H:25]5[N:29]([CH3:37])[C@@H:22]([CH2:23][CH2:24]5)[CH2:21]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 53377611HCID 53377611, compound

Product 1

HCID 67356062HCID 67356062, compoundYield 80%

Procedure

Following general reductive alkylation method 1, 7-Cyclopentyl-2-[5-((1S,6R)-4-oxo-3,9-diaza-bicyclo[4.2.1]non-3-yl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide was combined with formaldehyde (37% solution in water) which after purification gave 7-cyclopentyl-2-[5-((1S,6R)-9-methyl-4-oxo-3,9-diaza-bicyclo[4.2.1]non-3-yl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (41 mg) in 80% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.69 (s, 1H), 8.81 (s, 1H), 8.31 (d, J=9.09 Hz, 1H), 8.12 (d, J=2.53 Hz, 1H), 7.58 (dd, J=9.09, 2.53 Hz, 1H), 6.63 (s, 1H), 4.76 (m, 1H), 4.16 (d, J=14.65 Hz, 1H), 3.35 (m, 1H), 3.28 (m, 1H), 3.20 (t, J=6.57 Hz, 1H), 3.06 (br. s., 6H), 2.99 (m, 1H), 2.46 (m, 2H), 2.34 (s, 3H), 2.06 (m, 6H), 1.81 (m, 2H), 1.67 (m, 3H).

Workup

  1. customafter purification

Sources & evidence

ORD record
ord-d8ffb3001dbb416aae336641c205197f
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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