18621-18-6 → HCID 58315458, compound

HRID 1483076Notes

Reaction equation

HRID 1483076 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:22]([CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[Cl-].[OH:30][CH:31]1[CH2:34][NH2+:33][CH2:32]1>>[CH3:1][N:2]([CH3:28])[C:3]([C:5]1[N:22]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:33]4[CH2:34][CH:31]([OH:30])[CH2:32]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 4488865218621-18-6HCID 583154407-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

Product 1

HCID 58315458HCID 58315458, compoundYield 47%

Procedure

Following General Procedure B, 7-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide and 3-hydroxy-azetidinium chloride (73 mg, 0.667 mmol) gave 7-cyclopentyl-2-[5-(3-hydroxy-azetidin-1-ylmethyl)-pyridin-2-ylamino]-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a light yellow solid (0.131 g, 47%) [following SiO2 chromatography, eluting with 0-5% (2M NH3 in MeOH)/DCM). MS (ESI) m/z 436.2 (M+H)+ (method B).

Sources & evidence

ORD record
ord-22fc953be0644d4a944cd07b186862d2
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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