Diisopropylethylamine → HCID 71060508, compound

HRID 1036673Notes

Reaction equation

HRID 1036673 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[CH2:9]2)=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([NH:29][C:30]([CH3:50])([CH3:49])[C:31]([NH:33][C@H:34]([CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[N:41]([CH3:48])[CH:40]=1)[C:35](O)=[O:36])=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:12]3([CH2:17][CH2:16][CH2:15][N:14]([C:35](=[O:36])[C@H:34]([NH:33][C:31](=[O:32])[C:30]([NH:29][C:27](=[O:28])[O:26][C:22]([CH3:24])([CH3:23])[CH3:25])([CH3:50])[CH3:49])[CH2:38][C:39]4[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[N:41]([CH3:48])[CH:40]=4)[CH2:13]3)[C:11](=[O:18])[N:10]([CH:19]([CH3:21])[CH3:20])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 710602794-(4-Fluorophenyl)-2-(1-methylethyl)-2,7-diazaspiro[4.5]decan-1-oneHCID 71060485HCID 71060485, compound2×

Product 1

HCID 71060508HCID 71060508, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture comprising 4-(4-fluorophenyl)-2-isopropyl-2,7-diazaspiro[4.5]decan-1-one (ASW MedChem) (243 mg, 0.744 mmol), (R)-2-(2-(tert-butoxycarbonylamino)-2-methylpropanamido)-3-(1-methyl-1H-indol-3-yl)propanoic acid (Intermediate 3D) (300 mg, 0.744 mmol) and DIPEA (0.519 ml, 2.97 mmol) in acetonitrile (3 ml) was treated with ®T3P (50% in DMF, 0.868 ml, 1.487 mmol) and stirred at RT for 19 hours. The reaction mixture was concentrated in vacuo, dissolved in EtOAc and washed with water. The organic portion was dried (MgSO4) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 2% MeOH in DCM afforded the title compound;

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organic portion was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude product by chromatography on silica eluting with 2% MeOH in DCM

Sources & evidence

ORD record
ord-d43da3bbd4e944ed8678992567d416ca
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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