HCID 18536835, compound → HCID 18536936, compound

HRID 412967Notes

Reaction equation

COC1C=CC=CC=1S[C:10]1[S:14][C:13]([C:15]([NH2:17])=[NH:16])=[CH:12][C:11]=1[C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1.[CH3:29][O:30]C1C=CC=CC=1SC1SC(C(OC)=O)=CC=1C1SC=C(C2C=CC=CC=2)N=1>>[CH3:29][O:30][C:10]1[S:14][C:13]([C:15]([NH2:17])=[NH:16])=[CH:12][C:11]=1[C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:22]=1

Participants

Reactant 2

HCID 18536835HCID 18536835, compound

HCID 18537002HCID 18537002, compound

Product 1

HCID 18536936HCID 18536936, compoundYield 91%

Procedure

5-(Methyloxyphenylthio)-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamidine: Methyl 5-(methoxyphenylthio)-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate (100 mg, 0.22 mmol) was treated in a manner similar to that for Example 10, step (b), to give 5-methoxy-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxamidine (94 mg, 91%) as an orange solid. 1H-NMR (DMSO-d6; 300 MHz) δ 9.49 (br s, 2H), 9.15 (br s, 2H), 8.70 (s, 1H), 8.26 (s, 114), 8.07 (m, 214), 7.49 (m, 2H), 7.40 (m, 1H), 7.35 and 6.90 (AB quartet, 2H, J=8.7 Hz), 4.41 (s, 2H), 3.73 (s, 3H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C22H19N3OS3 438.5 (M+H), found 438.1.

Sources & evidence

ORD record: ord-10a72f6fd2064bd0a395c439c0555c63
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562840B1

Reaction notes

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