Benzylamine → HCID 59224407, compound

HRID 1672487Notes

Reaction equation

HRID 1672487 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([NH:11][C:12]3[N:13]=[CH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([C:22](O)=[O:23])=[CH:17][C:16]=4[CH3:25])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:57]([NH2:64])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CC(N(C)C)=O>[CH2:57]([NH:64][C:22]([C:18]1[CH:19]=[C:20]2[C:15](=[C:16]([CH3:25])[CH:17]=1)[CH:14]=[N:13][C:12]([NH:11][CH:8]1[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]1)=[CH:21]2)=[O:23])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58082125HCID 58082125, compound

Product 1

HCID 59224407HCID 59224407, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-8-methyl-isoquinoline-6-carboxylic acid (100.0 mg, 0.29 mmol) in 5 ml DMA was treated with a HATU (240.0 mg, 0.63 mmol) and triethylamine (192.0 mg, 1.89 mmol) for 1 hour at room temperature. After 1 hour, benzylamine (74.5 mg, 0.69 mmol) was added and the mixture was heated to 50° C. for 2 hours. The reaction was completed by LC/MS monitoring. The solvent DMA was evaporated under vacuum, and the crude was dissolved in CH2Cl2 and washed with NaHCO3 aqueous (10%) to remove the by-products from HATU. The crude residue was purified by a silica gel column to give 119.0 mg (94.4%). 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.59-1.75 (m, 2H), 1.78-1.95 (m, 4H), 2.01-2.12 (m, 2H), 2.64 (s, 3H), 3.39-3.55 (m, J=4.28 Hz, 1H), 3.91-4.04 (m, 4H), 4.69 (d, J=5.54 Hz, 2H, 6.62 (s, 1H), 6.94 (s, 1H), 7.34-7.46 (m, 5H), 7.87 (s, 1H), 8.85 (s, 1H).

Workup

  1. customThe solvent DMA was evaporated under vacuum
  2. dissolutionthe crude was dissolved in CH2Cl2
  3. washwashed with NaHCO3 aqueous (10%)
  4. customto remove the by-products from HATU
  5. customThe crude residue was purified by a silica gel column
  6. customto give 119.0 mg (94.4%)

Sources & evidence

ORD record
ord-310a03c972b64081b45e483fb724bddb
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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