Trifluoroacetic acid → 4-(4-Amino-quinazolin-7-ylmethyl)-2-(S)-methoxymethyl-3-oxo-piperazine-1-carboxylic acid (4-chloro-phenyl)-amide

HRID 1432983Notes

Reaction equation

HRID 1432983 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH2:19][O:20][CH3:21])[C:14]3=[O:22])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1.C(O)(C(F)(F)F)=O>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][C:8]3[CH:7]=[C:6]4[C:11]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)=[CH:10][CH:9]=3)[C:14](=[O:22])[C@@H:15]2[CH2:19][O:20][CH3:21])=[O:32])=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 76934-Chlorophenyl IsocyanateHCID 179852231-(4-Amino-quinazoline-7-ylmethyl)-3-methoxymethyl-piperazine-2-one

Product 1

HCID 539092944-(4-Amino-quinazolin-7-ylmethyl)-2-(S)-methoxymethyl-3-oxo-piperazine-1-carboxylic acid (4-chloro-phenyl)-amide

Procedure

The title compound is prepared as described in EXAMPLE 436 using 1-(4-amino-quinazoline-7-ylmethyl)-3-methoxymethyl-piperazine-2-one, EXAMPLE 75, and 4-chlorophenyl isocyanate. 1H NMR (DMSO-d6, 300 MHz) δ9.77 (bs, 2H), 8.81 (s, 1H), 8.70 (s, 1H), 8.40 (d, 1H), 7.64 (d, 1H), 7.61 (s, 1H), 7.49 (d, 2H), 7.28 (d, 2H), 4.88 (m, 1H), 4.80 (AB, 2H), 4.19 (m, 1H), 3.96 (m, 1H), 3.74-3.42 (m, 4H), 3.28 (s, 3H). ESI MS, [M+H]+=455,457 (Cl pattern). Anal. (C22H23ClN6O3.TFA.1.5H2O) C, H, N.

Sources & evidence

ORD record
ord-b6ef8c62420c4e4792e3289df1f143d5
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…