3-Amino-1,2-propanediol → N2-[3-[N-(2,3-dihydroxypropyl)amino]carbonylmethyleneaminophenyl]-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine

HRID 71562

Reaction equation

HRID 71562 reaction equation
C(C=N[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][CH2:27][CH2:28][OH:29])[CH:21]=2)[C:16]([F:30])=[CH:15][N:14]=1)(O)=O.[NH2:31][CH2:32][CH:33]([OH:36])[CH2:34][OH:35]>>[OH:36][CH:33]([CH2:34][OH:35])[CH2:32][NH:31][C:28]([CH:27]=[N:26][C:11]1[CH:6]=[C:7]([NH:12][C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][CH2:27][CH2:28][OH:29])[CH:21]=3)[C:16]([F:30])=[CH:15][N:14]=2)[CH:8]=[CH:9][CH:10]=1)=[O:29]

Participants

3

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 22060959N2-(carboxymethyleneaminophenyl)-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine

Product 1

HCID 57472944N2-[3-[N-(2,3-dihydroxypropyl)amino]carbonylmethyleneaminophenyl]-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N4-[3-(2-hydroxyethylamino)phenyl]-N2-[3-[N-(2-hydroxyethylamino)]carbonylmethyleneaminophenyl]-5-fluoro-2,4-pyrimidinediamine, N2-(carboxymethyleneaminophenyl)-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine and 1-amino-2,3-propanediol were reacted to give N2-[3-[N-(2,3-dihydroxypropyl)amino]carbonylmethyleneaminophenyl]-5-fluoro-N4-[3-(2-hydroxyethylamino)phenyl]-2,4-pyrimidinediamine. LCMS: ret. time: 12.86 min.; purity: 90.0%; MS (m/e): 486.40 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-db3e3aa842e2434380dbebc92ae2a438
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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