Hydrogen Bromide → HCID 53242175, compound

HRID 1521756Notes

Reaction equation

HRID 1521756 reaction equation
[CH3:1][C:2]1([CH3:20])[N:11]2[C:7](=[N:8][C:9]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][C:10]=32)[C:6](=[O:19])[NH:5][CH2:4][CH2:3]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:54][CH:55]([N:57]1[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=2[N:59]=[C:58]1[NH2:66])[CH3:56].Br.C(N(CC)CC)C>CN(C=O)C>[CH3:20][C:2]1([CH3:1])[N:11]2[C:7](=[N:8][C:9]3[CH:15]=[CH:14][C:13]([C:16]([NH:66][C:58]4[N:57]([CH:55]([CH3:56])[CH3:54])[C:61]5[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=5[N:59]=4)=[O:18])=[CH:12][C:10]=32)[C:6](=[O:19])[NH:5][CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 260Hydrogen Bromide2×HCID 8471TriethylamineHCID 2724699PyBOPHCID 27731961H-Benzimidazol-2-amine,1-(1-methylethyl)-(9CI)HCID 67245777HCID 67245777, compound2×

Product 1

HCID 53242175HCID 53242175, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5,5-dimethyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid (Intermediate C, 45 mg, 0.16 mmol) and PyBOP (145 mg, 0.28 mmol) in DMF (1.5 mL) is stirred for 10 min. 1-(Propan-2-yl)-1H-benzimidazol-2-amine; hydrobromide (Intermediate M, 71 mg, 0.28 mmol) and triethylamine (0.08 mL, 0.56 mmol) are added and the reaction is stirred for 16 h. The mixture is purified via preparative HPLC to afford the title compound (35 mg, 50%).

Workup

  1. customThe mixture is purified via preparative HPLC

Sources & evidence

ORD record
ord-96bc91ad3eb34c92a89931dfa04fff80
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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