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Sodium borohydride → 3-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-(hydroxymethyl)pyridin-2-yl)benzoic acid

HRID 2420930
Notes
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Reaction equation

HRID 2420930 reaction equation
[BH4-].[Na+].[F:3][C:4]1([F:38])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]([NH:18][C:19]4[N:24]=[C:23]([C:25]5[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=5)[C:28]([OH:30])=[O:29])[C:22]([C:34](OC)=[O:35])=[CH:21][CH:20]=4)=[O:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1>C1COCC1>[F:38][C:4]1([F:3])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]([NH:18][C:19]4[N:24]=[C:23]([C:25]5[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=5)[C:28]([OH:30])=[O:29])[C:22]([CH2:34][OH:35])=[CH:21][CH:20]=4)=[O:17])[CH2:14][CH2:15]3)=[CH:12][C:6]=2[O:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 591659443-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acid

Product 1

HCID 591661043-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-(hydroxymethyl)pyridin-2-yl)benzoic acidYield 40%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

NaBH4 (53 mg, 1.4 mmol) was added to a solution of 3-(6-(1-(2,2-difluorobenzo-[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acid (140 mg, 0.28 mmol) in THF (3 mL). The reaction was stirred at 50° C. for 5 hours. Additional NaBH4 (53 mg, 1.4 mmol) was added and the reaction was stirred at 50° C. overnight. The reaction was quenched by the addition of water and the reaction mixture was partitioned between CH2Cl2 and 1N HCl. The organic layer was dried (MgSO4) and concentrated. CH2Cl2 was added to the residue and a precipitate formed which was filtered to obtain the product as a white solid (52 mg, 40%). ESI-MS m/z calc. 468.1, found 469.5 (M+1)+. Retention time 1.64 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.10 (s, 1H), 8.06 (d, J=1.5 Hz, 1H), 8.01-7.93 (m, 3H), 7.76 (d, J=7.5 Hz, 1H), 7.57-7.54 (m, 2H), 7.40-7.34 (m, 2H), 5.33 (s, 1H), 4.38 (s, 2H), 1.53-1.51 (m, 2H), 1.19-1.16 (m, 2H).

Workup

  1. stirringthe reaction was stirred at 50° C. overnight
  2. customThe reaction was quenched by the addition of water
  3. customthe reaction mixture was partitioned between CH2Cl2 and 1N HCl
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. additionCH2Cl2 was added to the residue
  7. customa precipitate formed which
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-9e967a72cb484ff89fa51cd6a7fed0a6
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07956052B2

Reaction notes

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