Methanol → HCID 136348441, compound

HRID 1748773Notes

Reaction equation

HRID 1748773 reaction equation
[CH2:1]([N:3]1[C:7]2[NH:8][CH:9]([CH3:24])[CH2:10][S:11][CH:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][OH:22])=[CH:15][C:14]=3[CH3:23])[C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:4]1)[CH3:2].CO>[Pd].C1COCC1>[CH2:1]([N:3]1[C:7]2[NH:8][CH:9]([CH3:24])[CH2:10][S:11][CH:12]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][C:14]=3[CH3:23])[C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 136348442HCID 136348442, compound

Product 1

HCID 136348441HCID 136348441, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a flask was added 3-(4-(1-ethyl-7-methyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylphenyl)prop-2-yn-1-ol (0.126 g, 0.301 mmol, prepared from P with Example #K.1 and prop-2-yn-1-ol), MeOH (7.53 ml) and THF (7.53 ml). The solution was treated with the H-Cube (Pd/C 10 wt %, Manual Control, 20 bar, 1 mL/min, rt) for about 2 h. The mixture was concentrated in vacuo and purified by flash chromatography (25 g silica gel; DCM/MeOH 1:0 to 9:1) to give 3-(4-(1-ethyl-7-methyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylphenyl)propan-1-ol (0.110 g, 86%); LC-MS (Table 1, Method g) Rt=2.29 and 2.32 min.; MS m/z: 423.14 and 423.14 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by flash chromatography (25 g silica gel; DCM/MeOH 1:0 to 9:1)

Sources & evidence

ORD record
ord-93b655815f494b00967465657c1e6309
Source dataset
uspto-grants-2015_10
Patent number
US09150592B2

Reaction notes

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