Diisopropylethylamine → Tert-butyl 3-(1-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2-methoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 2042695Notes

Reaction equation

HRID 2042695 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:45]=[CH:44][C:19]([CH2:20][NH:21][C:22]2[N:27]=[C:26]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[N:25]=[C:24]([NH:34][C:35]3[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=3)[N:23]=2)=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:46][CH:47]([CH:52]1[CH2:57][CH2:56][CH2:55][N:54]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:53]1)[C:48]([O:50][CH3:51])=[O:49].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:45]=[CH:44][C:19]([CH2:20][NH:21][C:22]2[N:27]=[C:26]([O:28][CH2:29][C:30]([F:31])([F:32])[F:33])[N:25]=[C:24]([NH:34][C:35]3[CH:43]=[CH:42][C:38]([C:39]([NH:46][CH:47]([CH:52]4[CH2:57][CH2:56][CH2:55][N:54]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:53]4)[C:48]([O:50][CH3:51])=[O:49])=[O:40])=[CH:37][CH:36]=3)[N:23]=2)=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 24729647tert-butyl 3-((methoxycarbonyl)(amino)methyl)piperidine-1-carboxylateHCID 670742404-(4-(4-(6-(Tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

Product 1

HCID 67074083Tert-butyl 3-(1-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2-methoxy-2-oxoethyl)piperidine-1-carboxylateYield 57.1%

Procedure

To a solution of 4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (100 mg), tert-butyl 3-(1-amino-2-methoxy-2-oxoethyl)piperidine-1-carboxylate (51.5 mg) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium tetrafluoroborate (60.7 mg) was added iPr2NEt (0.055 mL). The mixture was stirred at room temperature for 4 hours. The mixture was purified by preparative HPLC to give tert-butyl 3-(1-(4-(4-(4-(6-(tert-butoxycarbonylamino)hexyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2-methoxy-2-oxoethyl)piperidine-1-carboxylate (80 mg).

Workup

  1. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-207dfce240bb4f2dac5ff8e34c290344
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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