Methanol → HCID 117902631, compound

HRID 1772166Notes

Reaction equation

HRID 1772166 reaction equation
Cl[C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[C:17]([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=3)=[O:21])[N:16]=[C:15]([NH:29][C:30]([CH:32]([N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH3:33])=[O:31])[CH:14]=2)[C:5]2[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:43][O-:44].[Na+].CO>O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]([NH:19][C:17]2[N:16]=[C:15]([NH:29][C:30]([CH:32]([N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[CH3:33])=[O:31])[CH:14]=[C:13]([C:4]3[C:5]4[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:6]=4[N:7]=[C:2]([O:44][CH3:43])[N:3]=3)[CH:18]=2)=[O:21])=[N:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 117902856HCID 117902856, compound

Product 1

HCID 117902631HCID 117902631, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl N-{1-[(4-{5-chloro-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl}-6-(5-chloropyridine-2-amido)pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate K63a (54 mg, 88 μmol), sodium methoxide (24 mg, 439 μmol) and methanol (400 μl) is stirred at 50° C. for 70 minutes. At RT water (10 ml) is added and the mixture extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 30 mg (56%). HPLC-MS: M+H=610; tR=1.12 min (METHOD—2).

Workup

  1. extractionthe mixture extracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-3a749a2d88b04427874e0cb15b73ab4a
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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