Potassium tert-butoxide → 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid

HRID 712291Notes

Reaction equation

HRID 712291 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([C:9]1([C:41]([O:43]CC)=[O:42])[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23](/[C:36](/[CH3:40])=[N:37]/[O:38][CH3:39])[C:24]4[S:28][C:27]([NH:29][C:30](=[O:34])[NH:31][CH2:32][CH3:33])=[N:26][C:25]=4[CH:35]=3)=[CH:17][N:16]=2)[CH2:11][CH2:10]1)[CH3:8]>CS(C)=O>[CH2:7]([C:9]1([C:41]([OH:43])=[O:42])[CH2:14][CH2:13][N:12]([C:15]2[N:16]=[CH:17][C:18]([C:21]3[CH:22]=[C:23](/[C:36](/[CH3:40])=[N:37]/[O:38][CH3:39])[C:24]4[S:28][C:27]([NH:29][C:30](=[O:34])[NH:31][CH2:32][CH3:33])=[N:26][C:25]=4[CH:35]=3)=[CH:19][N:20]=2)[CH2:11][CH2:10]1)[CH3:8]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 87222481HCID 87222481, compound

Product 1

HCID 872225094-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acidYield 25%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tertiary butoxide (71 mg, 0.63 mmol) was added to a solution of ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (87 mg, 0.16 mmol) in DMSO (1.5 mL). The mixture was stirred at rt 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 to give Compound 116 as a white solid, 27 mg, 25% yield. 1H NMR (DMSO-d6): δ 12.49 (1H, s), 10.66 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.58 Hz), 7.76 (1H, d, J=1.64 Hz), 6.94 (1H, t, J=5.58 Hz), 4.49 (2H, dt, J=13.57, 3.98 Hz), 4.10 (3H, s), 3.30-3.15 (4H, m), 2.42 (3H, s), 2.10 (2H, dt, J=13.97, 2.91 Hz), 1.57 (2H, q, J=7.49 Hz), 1.38 (2H, ddd, J=13.34, 11.14, 4.02 Hz), 1.14 (3H, t, J=7.17 Hz), 0.85 (3H, t, J=7.43 Hz). MS: 526 [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-5153154c87944becab246736cd738894
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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