Chlorosuccinimide → HCID 135998744, compound

HRID 1913266Notes

Reaction equation

HRID 1913266 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[OH:9][C@H:10]([CH3:43])[C:11]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:24]3[CH:25]=[CH:26][NH:27][C:23]=3[N:22]3[N:28]=[CH:29][C:30]([C:31]4[CH:32]=[N:33][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:35][CH:36]=4)=[C:21]3[N:20]=2)[CH2:15][CH2:14]1)=[O:12]>CN(C=O)C>[Cl:8][C:25]1[C:24]2[C:19]([CH:16]3[CH2:15][CH2:14][N:13]([C:11](=[O:12])[C@H:10]([OH:9])[CH3:43])[CH2:18][CH2:17]3)=[N:20][C:21]3[N:22]([N:28]=[CH:29][C:30]=3[C:31]3[CH:32]=[N:33][C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:35][CH:36]=3)[C:23]=2[NH:27][CH:26]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 135998730HCID 135998730, compound

Product 1

HCID 135998744HCID 135998744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NCS (3.7 mg, 0.027 mmoL) was added to a solution of (R)-2-hydroxy-1-(4-(3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)piperidin-1-yl)propan-1-one (25, prepared in Example 15) (12.8 mg, 0.027 mmoL) in DMF (1 mL). The mixture was stirred at room temperature for 3 days. Purification by prep-LC afforded (R)-1-(4-(6-chloro-3-(6-phenylpyridin-3-yl)-8H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidin-5-yl)piperidin-1-yl)-2-hydroxypropan-1-one (34): LCMS tR=3.70 Min (10 min run, UV254nm). Mass calculated for, M+500.1, observed 501.5 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-1128c8c59a64498f8581747f375c8d09
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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