Diisopropylethylamine → Ammonium Hydroxide

HRID 1027887Notes

Reaction equation

HRID 1027887 reaction equation
FC(F)(F)C(O)=[O:4].[CH2:8]([N:15]1[CH2:23][CH2:22][CH2:21][C:17]2([CH2:20][NH:19][CH2:18]2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC1C=CC(S(O[C:35]2[C:36]3[CH2:46][CH2:45][CH2:44][C:43]4[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=4[C:37]=3[N:38]=[C:39]([NH2:41])[N:40]=2)(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C>COCCO.C(Cl)Cl>[OH-:4].[NH4+:15].[CH2:8]([N:15]1[CH2:23][CH2:22][CH2:21][C:17]2([CH2:20][N:19]([C:35]3[C:36]4[CH2:46][CH2:45][CH2:44][C:43]5[CH:47]=[CH:48][CH:49]=[CH:50][C:42]=5[C:37]=4[N:38]=[C:39]([NH2:41])[N:40]=3)[CH2:18]2)[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonateHCID 692261806-Benzyl-2,6-diazaspiro[3.5]nonane 2,2,2-trifluoroacetate

Product 2

HCID 14923Ammonium HydroxideHCID 692254774-(6-benzyl-2,6-diazaspiro[3.5]non-2-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
115 °C

Procedure

The product from Example 77A was mixed with the product from Example 59C (135 mg, 0.35 mmol) in 2-methoxyethanol (1.2 mL) and N,N-diisopropylethylamine (0.74 mL, 1.74 mmol), then heated at 115° C. overnight, then cooled, diluted with CH2Cl2, and washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel, eluting with a gradient of 1:0 to 1:2 CH2Cl2:[10% (9:1 MeOH:saturated aqueous ammonium hydroxide)] to provide the title compound. MS (M+H)+ m/z 426.

Workup

  1. temperaturecooled
  2. washwashed with 1 M NaOH
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel
  8. washeluting with a gradient of 1:0 to 1:2 CH2Cl2

Sources & evidence

ORD record
ord-206b34b43679486d8a4bbe477d93800d
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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