Diisopropylethylamine → HCID 86691682, compound

HRID 1407045Notes

Reaction equation

HRID 1407045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]3[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]([NH:24][C:25]4[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][C:26]=4[F:34])[N:13]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:35][CH2:36][C:37]([CH3:48])([CH3:47])[CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]3[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])[N:15]=[C:14]([NH:24][C:25]4[CH:33]=[CH:32][C:28]([C:29]([NH:35][CH2:36][C:37]([CH3:48])([CH3:47])[CH2:38][NH:39][C:40](=[O:46])[O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:30])=[CH:27][C:26]=4[F:34])[N:13]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4114359tert-butyl N-(3-amino-2,2-dimethylpropyl)carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86691683HCID 86691683, compound

Product 1

HCID 86691682HCID 86691682, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-3-fluorobenzoic acid (200 mg, 0.42 mmol) in DCM (3 mL) was added tert-butyl 3-amino-2,2-dimethylpropylcarbamate (98 mg, 0.48 mmol), HATU (229 mg, 0.60 mol) and iPr2NEt (0.35 mL, 2.00 mmol). The mixture was stirred at r.t. for 16 hours before all the solvents were removed under vacuum. All solvents were removed under vacuum and the residue was purified by silica gel column (EtOAC/Hexanes=20% to 40%) to give tert-butyl 3-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-3-fluorobenzamido)-2,2-dimethylpropylcarbamate (270 mg, 100%) as a white solid.

Workup

  1. customwere removed under vacuum
  2. customAll solvents were removed under vacuum
  3. customthe residue was purified by silica gel column (EtOAC/Hexanes=20% to 40%)

Sources & evidence

ORD record
ord-65ac34bfdc824689ba415ae9724054ca
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

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