Diisopropylethylamine → HCID 178477660, compound

HRID 1910270Notes

Reaction equation

HRID 1910270 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:28]([OH:30])=O)[C:9]2[NH:13][C:12]([NH:14][C:15]([C:17]3[N:18]=[CH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:16])=[N:11][C:10]=2[CH:27]=1)(=[O:5])=[O:4])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.S(O)(O)(=O)=O.[NH2:69][C:70]1[NH:71][CH:72]=[CH:73][N:74]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:28](=[O:30])[NH:69][C:70]2[NH:71][CH:72]=[CH:73][N:74]=2)[C:9]2[NH:13][C:12]([NH:14][C:15]([C:17]3[N:18]=[CH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:16])=[N:11][C:10]=2[CH:27]=1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178477661HCID 178477661, compound

Product 1

HCID 178477660HCID 178477660, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

62 mg (0.15 mmol) of 6-ethylsulfonyl-2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carboxylic acid and 200 mg (0.53 mmol) of HBTU were dissolved in 1.0 mL of DMF and 0.5 mL of DIEA and treated with 132 mg (1.0 mmol) of 2-aminoimidazole sulfate as described in general procedure A. After the reaction was complete, diluted with brine 10 (mL). The resulting solid was filtered, washed with water, EtOAc and dried under vacuum to produce 36 mg (57%) of isoquinoline-3-carboxylic acid [5-ethanesulfonyl-7-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 490 (M+1)+.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water, EtOAc
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d29008be18ba4faeb5a17d348086200b
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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