tert-butyl N-(4-aminobutyl)carbamate → HCID 68186050, compound

HRID 628969Notes

Reaction equation

HRID 628969 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=3[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[C@H:10]([CH2:25][C:26]([OH:28])=O)[N:9]=2)=[CH:4][CH:3]=1.CN(C(O[N:37]1N=N[C:39]2[CH:40]=[CH:41][CH:42]=[N:43][C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.NCCCCN[C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=3[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[C@H:10]([CH2:25][C:26]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:28])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67173666HCID 67173666, compound

Product 1

HCID 68186050HCID 68186050, compound

Procedure

A mixture of [(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetic acid (for a preparation see Reference compound G) (1.0 g, 2.5 mmol), HATU (1.9 g, 5 mmol) and DIPEA (0.88 ml, 5 mmol) was stirred for 80 minutes at room temperature, to this was added 1,1-dimethylethyl (4-aminobutyl)carbamate (1.05 ml, 5.0 mmol, available from Aldrich). The reaction mixture was stirred at room temperature for 2 h before it was concentrated. The residue was taken up in dichloromethane and washed with 1N HCl. The aqueous layer was extracted with dichloromethane twice. Organic layer was washed with 1N sodium hydroxide, followed by a saturated solution of sodium chloride, dried over sodium sulphate and concentrated. The residue was purified by flash-chromatography on silica using dichloromethane/methanol 95/5 to give the title compound as a yellow solid (1.2 g). LC/MS (Method D): rt=3.04 min.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 h before it
  2. concentrationwas concentrated
  3. washwashed with 1N HCl
  4. extractionThe aqueous layer was extracted with dichloromethane twice
  5. washOrganic layer was washed with 1N sodium hydroxide
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by flash-chromatography on silica

Sources & evidence

ORD record
ord-ef4323c4ed144d6db325e3e88a0897ed
Source dataset
uspto-grants-2016_04
Patent number
US09315487B2

Reaction notes

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