Potassium tert-butoxide → HCID 56953212, compound

HRID 712284Notes

Reaction equation

HRID 712284 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([NH:9][C:10]([C:12]1[C:20]2[S:19][C:18]([NH:21][C:22](=[O:26])[NH:23][CH2:24][CH3:25])=[N:17][C:16]=2[CH:15]=[C:14]([C:27]2[CH:28]=[N:29][C:30]([N:33]3[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([O:41]CC)=[O:40])[CH2:35][CH2:34]3)=[N:31][CH:32]=2)[CH:13]=1)=[O:11])[CH3:8]>CS(C)=O>[CH2:7]([NH:9][C:10]([C:12]1[C:20]2[S:19][C:18]([NH:21][C:22](=[O:26])[NH:23][CH2:24][CH3:25])=[N:17][C:16]=2[CH:15]=[C:14]([C:27]2[CH:28]=[N:29][C:30]([N:33]3[CH2:34][CH2:35][C:36]([CH3:44])([C:39]([OH:41])=[O:40])[CH2:37][CH2:38]3)=[N:31][CH:32]=2)[CH:13]=1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86663996HCID 86663996, compound

Product 1

HCID 56953212HCID 56953212, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert butoxide (67 mg, 0.59 mmol) was added to a solution of ethyl 1-[5-[7-(ethylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (78 mg, 0.147 mmol) in DMSO (1.5 mL). The mixture was stirred at ambient temperature for 2 h after which time LCMS indicated clean conversion to the acid. The mixture was filtered through cotton wool to remove solid particulates and purified by preparative HPLC. Compound 97 was obtained as a white solid, 44 mg, 75% yield. 1H NMR (DMSO-d6): δ 10.86 (1H, s), 8.88 (2H, s), 8.82 (1H, t, J=5.47 Hz), 8.12 (1H, d, J=1.57 Hz), 8.05 (1H, d, J=1.45 Hz), 7.14 (1H, t, J=5.61 Hz), 4.32 (2H, dt, J=13.66, 4.46 Hz), 3.24 (5H, p, J=6.88 Hz), 3.20-3.27 (2H, m), 2.06 (2H, dt, J=13.52, 3.72 Hz), 1.41 (2H, ddd, J=13.42, 10.06, 3.89 Hz), 1.24 (1H, s), 1.22 (3H, t, J=3.29 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.17 Hz). MS: 512 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through cotton wool
  2. customto remove solid particulates
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-81fa222b9d094b328e3d7a9c4d24353a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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