Thiourea, 2-naphthalenyl- (9CI) → HCID 18537206, compound

HRID 2186621Notes

Reaction equation

HRID 2186621 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[N:13]=[C:14]([NH:17]C(C2C=CC3C(=CC=CC=3)C=2)=O)[S:15][CH:16]=1.[Br:30]CC(C1C=C(C(OC)=S)SC=1C)=O.[CH:44]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=[CH:46][C:45]=1NC(N)=S>>[BrH:30].[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[N:13]=[C:14]([NH:17][C:46]2[CH:45]=[CH:44][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:47]=2)[S:15][CH:16]=1

Participants

4

Reactant 3

HCID 2829258Thiourea, 2-naphthalenyl- (9CI)HCID 22456143HCID 22456143, compoundHCID 86583828Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate

Product 1

HCID 18537206HCID 18537206, compoundYield 80%

Procedure

Methyl 5-methylthio-4-[2-(2-naphthoylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxylate hydrohromide: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (65 mg, 0.21 mmol) was allowed react with 2-napthylthiourea (42.4 mg) as described in Example 154, step (a) to give 82.5 mg (80% yield) of methyl 5-methylthio-4-[2-(2-naphthylamino)(1,3-thiazol-4-yl)]thiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.67 (s, 3H), 3.83 (s, 3 H), 7.31 (s, 1H), 7.50-7.67 (m, 4H), 7.93 (m, 1H), 8.15 (s, 1H), 8.31-8.35 (m, 1H), 8.46 (d, 1H, J=7.6), 10.22 (s, 1H)); Mass Spectrum (ESI) m/z calcd. for C20H16N2O2S3, 412.6 (M+H), found 413.1.

Sources & evidence

ORD record
ord-a89d6507035c4950acdbd27ea1c0926f
Source dataset
uspto-grants-2002_06
Patent number
US06403633B2

Reaction notes

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