Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 5-(2-{[4-(1H-Benzimidazol-2-ylamino)butyl]amino}-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl acetate

HRID 2213156Notes

Reaction equation

HRID 2213156 reaction equation
C(OC(=O)C[CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[N:11]([CH2:20][C:21]([O-])=[O:22])[C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2)(C)(C)C.F[C:30](F)(F)[C:31]([OH:33])=[O:32].[NH:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=[C:37]1[NH:45][CH2:46][CH2:47][CH2:48][CH2:49][NH2:50].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[C:31]([O:33][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[N:11]([CH2:20][C:21]([NH:50][CH2:49][CH2:48][CH2:47][CH2:46][NH:45][C:37]2[NH:36][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=3[N:38]=2)=[O:22])[C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2)(=[O:32])[CH3:30]

Participants

4

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2195546111-(2-tert-butoxy-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-5-ylacetateHCID 85797825n1-(1h-Benzimidazol-2-yl)butane-1,4-diamine(trifluoroacetate)

Product 1

HCID 219554205-(2-{[4-(1H-Benzimidazol-2-ylamino)butyl]amino}-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl acetate

Procedure

Coupling of 11-(2-tert-butoxy-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-5-ylacetate (66) with N1-(1H-benzimidazol-2-yl)butane-1,4-diamine (trifluoroacetate) (49) using HATU as coupling reagent, cleavage of the tert-butyl ester and purification of the resulting crude product by RP-MPLC afforded 94 mg; ESI-MS [M+H+]=512.25.

Workup

  1. customas coupling reagent, cleavage of the tert-butyl ester and purification of the resulting crude product
  2. customby RP-MPLC afforded 94 mg

Sources & evidence

ORD record
ord-efe884b3212a493f96315f30d50a4963
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Reaction notes

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