Triethylamine → t-Butyl (2-(5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidin]-1'-yl)-2-oxoethyl)carbamate

HRID 1411235Notes

Reaction equation

HRID 1411235 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:31]([NH:38][CH2:39][C:40](O)=[O:41])([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:40](=[O:41])[CH2:39][NH:38][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH2:11]3)[CH2:9][N:8]([C:15](=[O:16])[NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)[C:5]2=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71522964HCID 71522964, compound

Product 1

HCID 117650996t-Butyl (2-(5-bromo-1-((5-chlorothiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidin]-1'-yl)-2-oxoethyl)carbamateYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (40 mg, 0.097 mmol) obtained in Example 2 was dissolved in methylene chloride (1.0 mL). Thereafter, triethylamine (27.0 μL, 0.194 mmol), N-Boc glycine (20 mg, 0.116 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (22 mg, 0.116 mmol) were added to the above obtained solution at room temperature, and the obtained mixture was then stirred for 12 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with chloroform. The resultant was dried over anhydrous sodium sulfate and was then concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (22.0 mg, 40%) in the form of a white solid.

Workup

  1. extractionwas then extracted with chloroform
  2. dry with materialThe resultant was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated in vacuo
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a8af7786c06e47579e5307ffdf71bb70
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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