Ammonium formate → HCID 59060811, compound

HRID 47686Notes

Reaction equation

HRID 47686 reaction equation
[CH3:1][C:2]([Si:5]([CH3:46])([CH3:45])[O:6][C@H:7]([CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:8][N:9]([CH2:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([NH2:36])=[O:35])[CH:29]=3)[CH:24]=2)[O:19]1)CC1C=CC=CC=1)([CH3:4])[CH3:3].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:4][C:2]([Si:5]([CH3:46])([CH3:45])[O:6][C@H:7]([CH2:37][O:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:8][NH:9][CH2:17][C@H:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([NH2:36])=[O:35])[CH:29]=3)[CH:24]=2)[O:19]1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 590608044-((2R)-2-{[[(2S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-(phenyloxy)propyl](phenylmethyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)-2-pyridinecarboxamide

Product 1

HCID 59060811HCID 59060811, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-((2R)-2-{[[(2S)-2-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}-3-(phenyloxy)propyl](phenylmethyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)-2-pyridinecarboxamide (Example 89, 44 mg, 0.07 mmol) was added to a suspension of 10% Pd/C (44 mg) in methanol (3 mL). Ammonium formate (22 mg, 0.35 mmol, 5.0 eq.) was added, and the mixture was heated at reflux for 30 minutes. Solids were removed by filtration through Celite®, and the filtrate was concentrated in vacuo. The title compound was collected as a pale yellow oil (25 mg, 66%): 1H NMR (300 MHz, acetone-d6) δ8.58 (d, 1 H), 8.32 (d, 1 H), 7.96 (broad s, 1 H), 7.78 (dd, 1 H), 7.60-7.56 (m, 2 H), 7.30-7.24 (m, 2 H), 6.95-6.81 (m, 4 H), 6.80 (broad s, 1 H), 4.25-4.19 (m, 2 H), 4.15-4.07 (m, 1 H), 3.99-3.92 (m, 1 H), 2.99-2.86 (m, 6 H), 2.13-2.06 (m, 1 H), 1.90-1.80 (m, 1 H), 0.92 (s, 9 H), 0.16 (s, 3 H), 0.13 (s, 3 H); MS m/z 548.3 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. customSolids were removed by filtration through Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe title compound was collected as a pale yellow oil (25 mg, 66%)

Sources & evidence

ORD record
ord-aad580eacc584b5ea1b9157014233551
Source dataset
uspto-grants-2004_03
Patent number
US06699860B2

Reaction notes

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