HCID 58315419, compound → HCID 58315413, compound

HRID 1853156Notes

Reaction equation

HRID 1853156 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[CH:29]=[C:28]([C:30]#[N:31])[N:27]([CH:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(OCC)C>[CH:32]1([N:27]2[C:25]3[N:26]=[C:21]([NH:20][C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:15][N:16]=4)[N:22]=[CH:23][C:24]=3[CH:29]=[C:28]2[C:30]#[N:31])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 1

HCID 58315419HCID 58315419, compound

Product 1

HCID 58315413HCID 58315413, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using General Procedure A, 4-[6-(6-cyano-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester (20 mg) gave crude product which is purified by SCX column (eluting with a 1:17 mixture of 2M NH3 in MeOH/dichloromethane) to give a solid. Trituration with diethyl ether gave 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile (8.8 mg, 7%) (over 2 steps). MS (ESI) m/z 389.2 (M+H)+ (method A).

Workup

  1. customgave crude product which
  2. customis purified by SCX column (
  3. washeluting with a 1:17 mixture of 2M NH3 in MeOH/dichloromethane)
  4. customto give a solid

Sources & evidence

ORD record
ord-a44b93fc58454a5bb793da72c7c2a9d4
Source dataset
uspto-grants-2015_02
Patent number
US08962630B2

Reaction notes

Loading…