HCID 87222433, compound → HCID 87222515, compound

HRID 712276Notes

Reaction equation

HRID 712276 reaction equation
C(O[K])(C)(C)C.[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:28]=[N:29][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([O:41]CC)=[O:40])[CH2:35][CH2:34]4)=[N:31][CH:32]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]>CS(C)=O>[CH2:7]([NH:9][C:10]([NH:12][C:13]1[S:14][C:15]2[C:21](/[C:22](/[CH3:26])=[N:23]/[O:24][CH3:25])=[CH:20][C:19]([C:27]3[CH:32]=[N:31][C:30]([N:33]4[CH2:38][CH2:37][C:36]([CH3:44])([C:39]([OH:41])=[O:40])[CH2:35][CH2:34]4)=[N:29][CH:28]=3)=[CH:18][C:16]=2[N:17]=1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 87222433HCID 87222433, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 87222515HCID 87222515, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

tBuOK (124 mg, 1.11 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (4 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 to give Compound 88 as a white solid, 76 mg, 40% yield over 2 steps. 1H NMR (DMSO-d6): δ 10.89 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.62 Hz), 7.76 (1H, d, J=1.69 Hz), 7.16 (1H, t, J=5.50 Hz), 4.32 (2H, dt, J=13.67, 4.40 Hz), 4.09 (3H, s), 3.38 (2H, ddd, J=13.49, 10.48, 3.40 Hz), 3.23 (2H, p, J=6.71 Hz), 2.42 (3H, s), 2.05 (2H, dt, J=13.34, 3.66 Hz), 1.41 (2H, ddd, J=13.34, 10.04, 3.92 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.15 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-c049c60c51ae4d60aa26597ff75e326c
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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