Potassium Hydroxide → N-[Pyrrolidin-3-yl]-6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-amine

HRID 1910461Notes

Reaction equation

HRID 1910461 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[C:22]3[S:23][C:24]([CH3:26])=[CH:25][C:21]=3[N:20]=[C:19]([N:27]3[CH2:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[S:30](=[O:38])[CH2:29][CH2:28]3)[N:18]=2)[CH2:12]1)=O)C1C=CC=CC=1.[OH-].[K+]>CO>[NH:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17]2[C:22]3[S:23][C:24]([CH3:26])=[CH:25][C:21]=3[N:20]=[C:19]([N:27]3[CH2:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[S:30](=[O:38])[CH2:29][CH2:28]3)[N:18]=2)[CH2:12]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86680739Benzyl 3-{[2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthienopyrimidin-4-yl]amino}-pyrrolidine-1-carboxylate

Product 1

HCID 71548934N-[Pyrrolidin-3-yl]-6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl-3-{[2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthienopyrimidin-4-yl]amino}-pyrrolidine-1-carboxylate (300 mg, 0.55 mmol) in methanol (5 mL) was added an aqueous solution of potassium hydroxide (40%, 5 mL). The suspension was heated under reflux for 30 minutes. The organic solvent was removed by concentration in vacuo. The residue was purified by preparative HPLC to afford the pure product as a white solid. MS obsd. (ESI+) [(M+H)+] 414, 1H NMR (METHANOL-d4) δ ppm 7.73 (d, J=7.6 Hz, 1H), 7.68 (d, J=7.1 Hz, 1H), 7.37-7.52 (m, 2H), 6.77-6.85 (m, 1H), 5.19 (d, J=15.4 Hz, 1H), 4.79-4.97 (m, 3H), 4.71 (br. s., 1H), 3.44 (d, J=3.0 Hz, 2H), 3.25-3.38 (m, 2H), 3.21 (d, J=5.8 Hz, 1H), 3.02-3.13 (m, 1H), 2.54 (s, 3H), 2.34 (td, J=12.9, 6.9 Hz, 1H), 1.95-2.07 (m, 1H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. customThe organic solvent was removed by concentration in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-13a44d9b26b6475f901e6425653af0b8
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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