Sodium borohydride → HCID 57812596, compound

HRID 912003Notes

Reaction equation

HRID 912003 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[S:15][C:14]([CH:16]=[O:17])=[CH:13][CH:12]=3)=[CH:9][O:10][C:4]=2[C:3]=1[O:18][C@@H:19]([C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=1[Cl:29])[CH3:20].[BH4-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[S:15][C:14]([CH2:16][OH:17])=[CH:13][CH:12]=3)=[CH:9][O:10][C:4]=2[C:3]=1[O:18][C@@H:19]([C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=1[Cl:29])[CH3:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57812491HCID 57812491, compound

Product 1

HCID 57812596HCID 57812596, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-furo[3,2-c]pyridin-3-yl}-thiophene-2-carbaldehyde (6.0 mg, 0.013 mmol), sodium borohydride (2.5 mg, 0.067 mmol) and MeOH (1 mL) was stirred at 0° C. for 1 h. The material was concentrated in vacuo and redissolved in DMF (0.5 mL) for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.90 (d, J=6.8 Hz, 3H), 4.76 (s, 2H), 6.54 (q, J=6.8 Hz, 1H), 7.01 (d, J=3.5 Hz, 1H), 7.19-7.27 (m, 2H), 7.41 (dd, J=9.0, 4.9 Hz, 1H), 7.86 (s, 1H), 8.22 (s, 1H). MS (ES+): m/z 452.90 (100) [MH+]. HPLC: tR=3.27 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe material was concentrated in vacuo
  2. dissolutionredissolved in DMF (0.5 mL) for HPLC purification
  3. additionThe fractions containing the pure product
  4. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-c9612c4aae2e47708849ac7d9d85c7ab
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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