Trifluoroacetic acid → HCID 10074688, compound

HRID 1353492Notes

Reaction equation

HRID 1353492 reaction equation
CC(O[C:6](=[O:22])[NH:7][C@@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH:17][CH:18]2[CH2:20][CH2:19]2)=[O:16])[C:9]1=[O:21])(C)C.C(O)(C(F)(F)F)=O.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C([O-])(O)=O.[Na+].[Cl:47][C:48]1[CH:57]=[C:56]2[C:51]([C:52]([N:59]3[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]3)=[CH:53][C:54]([NH2:58])=[N:55]2)=[CH:50][CH:49]=1>>[NH2:58][C:54]1[CH:53]=[C:52]([N:59]2[CH2:60][CH2:61][N:62]([C:6]([NH:7][C@H:8]3[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C:15]([NH:17][CH:18]4[CH2:19][CH2:20]4)=[O:16])[C:9]3=[O:21])=[O:22])[CH2:63][CH2:64]2)[C:51]2[C:56](=[CH:57][C:48]([Cl:47])=[CH:49][CH:50]=2)[N:55]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 211017487-Chloro-4-(1-piperazinyl)-2-quinolinamineHCID 21101832HCID 21101832, compound

Product 1

HCID 10074688HCID 10074688, compound

Procedure

As described for example 213, [(3R)-1-[(cyclopropylamino)carbonyl]hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid-1,1-dimethylethyl ester, TFA, triphosgene, NaHCO3 (sat.), and 7-chloro-4-(1-piperazinyl)-2-quinolinamine are reacted to afford the product as a white solid. LC-MS: 500 (M++1). 1H NMR (CDCl3): δ 0.50˜0.62 (m, 2H), 0.72–0.84 (m, 2H), 1.42 (m, 1H), 1.60 (m, 1H), 1.82˜2.02 (m, 3H), 2.13 (m, 1H), 2.76 (ddd, 1H), 3.12 (br.dd, 4H), 3.24 (br.dd, 1H), 3.66 (m, 4H), 4.82˜4.94 (m, 2H), 5.02 (br.s, 2H), 5.86 (d, 1H), 6.16 (s, 1H), 7.16 (dd, 1H), 7.60 (d, 1H), 7.72 (d, 1H), 9.10 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-2514c615ddbb4689bb719fd282cee2dd
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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