1-Hydroxybenzotriazole → HCID 46926701, compound

HRID 1891109Notes

Reaction equation

HRID 1891109 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][S:9][C:10](C)=[C:6]2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[F:15][C:16]1[C:21]([F:22])=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:18][C:17]=1[C:27]1[N:28]=[C:29]([NH2:32])[S:30][CH:31]=1.CCN=C=NC[CH2:39][CH2:40]N(C)C.Cl.C1C=CC2N([OH:54])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[F:15][C:16]1[C:21]([F:22])=[C:20]([C:23]([F:26])([F:24])[F:25])[CH:19]=[CH:18][C:17]=1[C:27]1[N:28]=[C:29]([NH:32][C:39](=[O:54])[CH2:40][C:7]2[C:6]3[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:10]=3[S:9][CH:8]=2)[S:30][CH:31]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58026081HCID 58026081, compoundHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 46926701HCID 46926701, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 4-[2,3-difluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (110 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 27 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.08 (s, 2H), 7.08 (s, 1H), 7.70-7.80 (m, 2H), 7.98-8.04 (m, 1H), 12.56 (br s, 1H); APCI-MS (m/z) 517.06 (M+H)+.

Sources & evidence

ORD record
ord-78fcdec8b2e246d0ac4874ad5511a757
Source dataset
uspto-grants-2013_08
Patent number
US08507503B2

Reaction notes

Loading…