Chlorosuccinimide → HCID 22182413, compound

HRID 1432189Notes

Reaction equation

HRID 1432189 reaction equation
[N:1]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:4]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:3][CH:2]=1.[Cl:24]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:24][C:8]1[S:7][C:6]2[N:1]=[CH:2][N:3]=[C:4]([NH:10][CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]3)[C:5]=2[CH:9]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22182417HCID 22182417, compound

Product 1

HCID 22182413HCID 22182413, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of t-butyl 4-(thieno[2,3-d]pyrimidin-4-ylamino)piperidine-1-carboxylate (1.00 g, 3.00 mmol) and N-chlorosuccinimide (0.39 g, 3.00 mmol) were heated in 50 mL of acetic acid for 3 h. After cooling to room temperature acetic acid was removed under reduced pressure and the remaining residue was partition in 1 M NaOH and DCM. The DCM layer was dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica chromatography in 5% MeOH-DCM to collect 0.78 g of product (71% yield). 1H NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 7.01 (s, 1H), 4.94 (d, 1H), 4.32 (m, 1H), 4.15 (m, 2H), 2.94 (m, 2H), 2.11 (m, 2H), 1.48 (s, 9H), 1.44 (m, 2H); MS (ESI) m/z: Calculated for C16H21ClN4O2S, 368.11; Observed: 368.8 (M++1).

Workup

  1. customwas removed under reduced pressure
  2. customthe remaining residue was partition in 1 M NaOH
  3. dry with materialThe DCM layer was dried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by silica chromatography in 5% MeOH-DCM

Sources & evidence

ORD record
ord-e68cdbbb113e4618a033c793084dfdb4
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

Loading…