2-Thiophenecarboxaldehyde → HCID 86601764, compound

HRID 1162601Notes

Reaction equation

COC(=O)C1C=CC=[C:6]([NH2:10])C=1.[S:12]1C=CC=C1C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:33][O:34][C:35](=[O:49])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH:42][CH2:43][C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)[CH:37]=1>>[CH3:33][O:34][C:35](=[O:49])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([N:42]([CH2:43][C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)[C:6]([NH2:10])=[S:12])[CH:37]=1

Participants

Reactant 4

HCID 73642-Thiophenecarboxaldehyde

HCID 78274Benzoic acid, 3-amino-, methyl ester

HCID 5049666Sodium triacetoxyborohydride

HCID 43087835HCID 43087835, compound

Product 1

HCID 86601764HCID 86601764, compoundYield 89.6%

Procedure

3-Amino-benzoic acid methyl ester (455 mg, 3.0 mmol), thiophene carboxaldehyde (290 μL, 3.15 mmol) and sodium triacetoxyborohydride (765 mg, 3.6 mmol) were combined according to general procedure D. 189 mg of the crude 3-[(thiophen-2-ylmethyl)-amino]-benzoic acid methyl ester (0.75 mmol) was treated with 1 eq. Fmoc-NCS to afford 206 mg 3-(1-thiophen-2-ylmethyl-thioureido)-benzoic acid methyl ester after purification.

Sources & evidence

ORD record: ord-b9f59cba294244fbbe4c88926ae3df59
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820704B2

Reaction notes

Loading…