Diisopropylethylamine → HCID 66940566, compound

HRID 1910243Notes

Reaction equation

HRID 1910243 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[N:8][C:7]([C:15]([OH:17])=O)=[CH:6]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.[CH2:51]([O:53][C:54]([C:56]1[C:64]2[N:63]=[C:62]([NH2:65])[NH:61][C:60]=2[CH:59]=[C:58]([O:66][CH2:67][CH3:68])[CH:57]=1)=[O:55])[CH3:52]>CN(C=O)C.[Cl-].[Na+].O>[CH2:51]([O:53][C:54]([C:56]1[C:64]2[N:63]=[C:62]([NH:65][C:15]([C:7]3[N:8]=[CH:9][C:10]4[C:5]([CH:6]=3)=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=4)=[O:17])[NH:61][C:60]=2[CH:59]=[C:58]([O:66][CH2:67][CH3:68])[CH:57]=1)=[O:55])[CH3:52]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14278968HCID 14278968, compoundHCID 66940226HCID 66940226, compound

Product 1

HCID 66940566HCID 66940566, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

235 mg (1.0 mmol) of 6,7-dimethoxy-isoquinoline-3-carboxylic acid and 400 mg (1.0 mmol) of HBTU were dissolved in 1.5 mL of DMF and 0.5 mL of DIEA and treated with 249 mg (1.0 mmol) of 2-amino-6-ethoxy-1H-benzoimidazole-4-carboxylic acid ethyl ester (prepared in Example 471) as described in general procedure A. Upon completion, the reaction was diluted with brine. The resulting solid was filtered, washed with water and EtOAc, and dried under vacuum to produce 290 mg (0.63 mmol, 63%) of 2-[(6,7-dimethoxy-isoquinoline-3-carbonyl)-amino]-6-ethoxy-1H-benzoimidazole-4-carboxylic acid ethyl ester. LCMS: 465 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-f31fdef647e94ff4b2a3aedd489bad4c
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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