HCID 86760981, compound → HCID 57029141, compound

HRID 1432985Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][N:20]3[CH2:25][C@H:24]([CH3:26])[N:23]([CH2:27][CH:28]=[CH:29][C:30]4[S:31][C:32]([Cl:35])=[CH:33][CH:34]=4)[C@@H:22]([CH3:36])[C:21]3=[O:37])=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1.FC(F)(F)C(O)=O.NC1C2C(=CC(CN3C[C@@H](C)N(CC=CC4SC(Cl)=CC=4)[C@@H](C)C3=O)=CC=2)N=CN=1>>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][N:20]3[CH2:25][C@@H:24]([CH3:26])[N:23]([CH2:27][CH:28]=[CH:29][C:30]4[S:31][C:32]([Cl:35])=[CH:33][CH:34]=4)[C@@H:22]([CH3:36])[C:21]3=[O:37])=[CH:16][CH:17]=2)[N:12]=[CH:11][N:10]=1

Participants

Reactant 2

HCID 86760981HCID 86760981, compound

HCID 86760982HCID 86760982, compound

Product 1

HCID 57029141HCID 57029141, compound

Procedure

The major epimer is assigned as (3S, 5S)-1-(4-Amino-quinazolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazin-2-one trifluoroacetic acid salt (30.8 mg) and is isolated as a yellow solid with a melting point of 69-72° C. C22H24ClN5OS MS m/z: 442, 444. The minor epimer is assigned as (3S, 5R)-1-(4-Amino-quinazolin-7-ylmethyl)-4-[3-(5-chloro-thiophen-2-yl)-allyl]-3,5-dimethyl-piperazin-2-one trifluoroacetic acid salt (13.1 mg) with a melting point of 67-70° C. C22H24ClN5OS MS m/z: 442, 444. 1H NMR (CD3OD) δ: 8.67 (s, 1H); 8.31 (d, 1H, J=8.56 Hz); 7.83 (s, 1H); 7.74 (d, 2H, J=8.56 Hz); 7.14 (d, 1H, J=15.6 Hz); 6.92 (d, 1H, J=3.74 Hz); 6.10-6.03 (m, 1H); 5.0-4.74 (m, 2H); 4.25-3.63 (m, 6H); 1.78 (d, 3H, J=7.03 Hz); 1.50 (d, 3H, J=6.47 Hz).

Workup

customis isolated as a yellow solid with a melting point of 69-72° C

Sources & evidence

ORD record: ord-306e1e4b8825493fb8468cfda54836ed
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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