Beta-Alanine → HCID 11236397, compound

HRID 2220270Notes

Reaction equation

HRID 2220270 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([CH:18]=O)[CH:16]=[CH:17][C:11]=3[CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].CCN(CC)CC.[BH4-].[Na+]>CO>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[C:7]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([CH2:18][NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:16]=[CH:17][C:11]=3[CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 86596036HCID 86596036, compound

Product 1

HCID 11236397HCID 11236397, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene-6-carbaldehyde(23 mg, 0.05 mmol) in 3 mL MeOH, β-alanine (8.7mg, 0.1 mmol) and catalytic amount Et3N are added. The suspension is heated to 50° C. for 0.5 hours, followed by the addition of 2 mg of NaBH4. After Pre-LC-MS, 10 mg of 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophen-6-ylmethyl]-amino}-propionic acid is obtained as a white solid. MS m/z 456[M+1]+. 1H NMR (MeOD-d4): δ 8.22 (d, 1H), 7.93 (m, 2H), 7.86 (d, 1H), 7.81 (s, 1H), 7.40 (m, 1H), 7.34 (d, 1H), 7.28 (m, 3H), 7.24 (m, 2H), 4.26 (s, 2H), 3.15 (t, 2H), 2.52 (t, 2H).

Sources & evidence

ORD record
ord-2e8ac7fef42f47968efa796b5b6ead61
Source dataset
uspto-grants-2008_08
Patent number
US07417065B2

Reaction notes

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