tert-butyl N-(4-aminobutyl)carbamate → HCID 67074087, compound

HRID 2042687Notes

Reaction equation

HRID 2042687 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:9][C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])[N:13]=[C:12]([NH:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[N:11]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[NH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37]C(=O)OC(C)(C)C.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>CN(C=O)C>[NH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:27]([C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:12]2[N:13]=[C:14]([O:16][CH2:17][C:18]([F:20])([F:21])[F:19])[N:15]=[C:10]([NH:9][C:6]3([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:7]3)[N:11]=2)=[CH:31][CH:30]=1)=[O:28]

Participants

6

Reactant 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67074718HCID 67074718, compound

Product 1

HCID 67074087HCID 67074087, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-(1-(ethoxycarbonyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (100 mg) in DMF (5 mL) was added tert-butyl 4-aminobutylcarbamate (64.0 mg), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (109 mg) and iPr2NEt (0.119 mL). The mixture was stirred at r.t. for 16 hours before all the solvents were removed under vacuum. The residue was dissolved in dichloromethane (5.00 mL) and 2 mL of TFA. The mixture was stirred at r.t. for 3 hours. All solvents were removed under vacuum and the residue was purified by prep. HPLC to give ethyl 1-(4-(4-(4-aminobutylcarbamoyl)phenylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)cyclopropanecarboxylate (80 mg).

Workup

  1. customwere removed under vacuum
  2. dissolutionThe residue was dissolved in dichloromethane (5.00 mL)
  3. stirringThe mixture was stirred at r.t. for 3 hours
  4. customAll solvents were removed under vacuum
  5. customthe residue was purified by prep

Sources & evidence

ORD record
ord-42802ec539fd48b7910a11adc6852655
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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