Propylphosphonic anhydride → HCID 118671962, compound

HRID 630492Notes

Reaction equation

HRID 630492 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([OH:25])=O)[CH:21]=3)[C:16]([S:26]([CH3:28])=[O:27])=[CH:15]2)=[N:12][CH:13]=1.[CH:29]12[CH2:35][CH:32]([NH:33][CH2:34]1)[CH2:31][N:30]2C(OC(C)(C)C)=O.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>>[CH:29]12[CH2:35][CH:32]([NH:33][CH2:34]1)[CH2:31][N:30]2[C:23]([C:20]1[CH:21]=[C:22]2[C:17]([C:16]([S:26]([CH3:28])=[O:27])=[CH:15][N:14]2[C:11]2[N:12]=[CH:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[CH:9][N:10]=2)=[CH:18][CH:19]=1)=[O:25]

Participants

4

Reactant 3

HCID 111923Propylphosphonic anhydrideHCID 2760898(1S,4S)-tert-butyl 2,5-diazabicyclo(2.2.1)heptane-2-carboxylateHCID 1186660891-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid

Product 1

HCID 118671962HCID 118671962, compound

Procedure

Prepared from 1-(5-(2-fluorophenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indole-6-carboxylic acid and tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate in two steps comprising a T3P coupling and a TFA-catalyzed removal of the Boc protecting group. Light yellow solid.

Workup

  1. customa TFA-catalyzed removal of the Boc protecting group

Sources & evidence

ORD record
ord-627fd217e7fd4098a145e408955cfc91
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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