Diisopropylethylamine → HCID 90901986, compound

HRID 476301Notes

Reaction equation

HRID 476301 reaction equation
CCN(C(C)C)C(C)C.C1C=CC(OP(OC2C=CC=CC=2)([N:19]=[N+:20]=[N-:21])=O)=CC=1.[C:29]([O:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[CH:47]=[CH:46][C:45]([CH2:48][N:49]2[C:53]3[CH:54]=[C:55]([C:59](O)=[O:60])[CH:56]=[C:57]([CH3:58])[C:52]=3[N:51]=[C:50]2[CH2:62][CH2:63][CH3:64])=[CH:44][CH:43]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C.[Na+].[Cl-]>[C:29]([O:33][C:34]([C:36]1[C:37]([C:42]2[CH:43]=[CH:44][C:45]([CH2:48][N:49]3[C:53]4[CH:54]=[C:55]([C:59]([N:19]=[N+:20]=[N-:21])=[O:60])[CH:56]=[C:57]([CH3:58])[C:52]=4[N:51]=[C:50]3[CH2:62][CH2:63][CH3:64])=[CH:46][CH:47]=2)=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:35])([CH3:30])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 59868523HCID 59868523, compound

Product 1

HCID 90901986HCID 90901986, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.43 mL, 25 mmol) and diphenylphosphonic azide (489 μL, 2.3 mmol) were added to a solution of 3-(2′-t-butoxycarbonylbiphenyl-4-ylmethyl)-7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (1.0 g, 2.1 mmol; prepared as described in Preparation 3) in DMF (15 mL). The mixture was stirred at room temperature for 16 hours, diluted with saturated aqueous NaCl (100 mL), then extracted with EtOAc (200 mL). The organic layer was evaporated to dryness to yield crude Intermediate (10a). MS m/z: [M+H+] calcd for C30H31N5O3, 510.2. found 510.6.

Workup

  1. extractionextracted with EtOAc (200 mL)
  2. customThe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-aa1b98534d2f4a759465e2e91a240a17
Source dataset
uspto-grants-2014_01
Patent number
US08637676B2

Reaction notes

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