2-Amino-6-fluorobenzothiazole → HCID 46833853, compound

HRID 1882167Notes

Reaction equation

HRID 1882167 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20](O)=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.[F:30][C:31]1[CH:40]=[CH:39][C:34]2[N:35]=[C:36]([NH2:38])[S:37][C:33]=2[CH:32]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([NH:38][C:36]2[S:37][C:33]4[CH:32]=[C:31]([F:30])[CH:40]=[CH:39][C:34]=4[N:35]=2)=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 3199542-Amino-6-fluorobenzothiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 46833853HCID 46833853, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (100 mg, 0.236 mmol) with 6-fluoro-1,3-benzothiazol-2-amine (44 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), DMAP (27 mg, 0.236 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 15 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 3.59 (s, 2H), 7.19 (t, J=74.7 Hz, 1H), 7.21-7.28 (m, 1H), 7.32-7.38 (m, 1H), 7.42-7.48 (m, 2H), 7.57-7.62 (m, 1H), 7.70-7.76 (m, 1H), 7.84-7.93 (m, 2H), 8.05-8.12 (m, 1H), 8.47-8.53 (m, 1H), 13.48 (br s, 1H); ESI-MS (m/z) 573.46 (MH)+.

Sources & evidence

ORD record
ord-9ac3db4f8e71497fa3a694f4f4f65957
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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