Propylamine → HCID 59578009, compound

HRID 2194230Notes

Reaction equation

HRID 2194230 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:11]2=[O:20])=[CH:6][CH:5]=1.CCN(CC)CC.O=C(Cl)[O:32][C:33](Cl)(Cl)Cl.[CH2:38]([NH2:41])[CH2:39][CH3:40]>C(Cl)Cl>[CH2:38]([NH:41][C:33]([N:17]1[CH2:16][CH2:15][C:12]2([C:11](=[O:20])[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=3)[CH2:14][CH2:13]2)[CH2:19][CH2:18]1)=[O:32])[CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 10426DiphosgeneHCID 667427592-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one

Product 1

HCID 59578009HCID 59578009, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 13.7 mg (0.06 mmol) 2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one and 24.2 mg (0.24 mmol) NEt3 in 2 mL CH2Cl2 at 0° C. was added 13 mg (0.066 mmol) diphosgene and stirred for 10 min. After addition of 10.6 mg (0.18 mmol) propylamine the mixture was stirred for 16 h at room temperature, evaporated to dryness and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 1.1 mg (5%) the title compound. MS (ESI): 400.3 (MH+).

Workup

  1. stirringwas stirred for 16 h at room temperature
  2. customevaporated to dryness
  3. custompurified by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and NEt3
  6. additionThe product containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-e2db7fb679bc47959ca086d56e431491
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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