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Isopropylamine → N-cyclopropylsulfonyl-13-methyl-2,14-dioxo-17-[2-(propan-2-ylamino)pyrimidin-4-yl]oxy-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

HRID 1429159
Notes
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Reaction equation

HRID 1429159 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=4)[CH2:20][CH:19]3[C:31]([N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=C)[CH3:34])=[O:32])=[O:17])[CH2:12][CH:11]2[CH:13]=C)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:41]([NH2:44])([CH3:43])[CH3:42]>C1COCC1.ClCCCl>[CH:41]([NH:44][C:26]1[N:25]=[C:24]([O:23][CH:21]2[CH2:22][CH:18]3[CH:19]([C:31](=[O:32])[N:33]([CH3:34])[CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH:13][CH:11]4[C:10]([C:8]([NH:7][S:4]([CH:1]5[CH2:3][CH2:2]5)(=[O:6])=[O:5])=[O:9])([NH:15][C:16]3=[O:17])[CH2:12]4)[CH2:20]2)[CH:29]=[CH:28][N:27]=1)([CH3:43])[CH3:42]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 72253694N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide

Product 1

HCID 75277257N-cyclopropylsulfonyl-13-methyl-2,14-dioxo-17-[2-(propan-2-ylamino)pyrimidin-4-yl]oxy-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxamide

Reagents, catalysts & solvents 2

HCID 11
1,2-Dichloroethane
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

Compound 10f (30 mg, 0.05 mmol) and isopropylamine (excess) in THF (10 ml) was heated in a microwave oven at 110° C. for 30 min and then left at ambient temperature for 16 hrs. The solvent was stripped of and the residue was redissolved in DCE (15 ml) and degassed with nitrogen. Hoyeda-Grubbs II catalyst (7 mg) was added and the mixture was heated in a microwave oven at 150° C. for 10 min. The mixture was concentrated to dryness and purified by prep. HPLC-MS-UV which gave the pure title compound (3.1 mg), (M+H)+=589.2.

Workup

  1. customdegassed with nitrogen
  2. additionHoyeda-Grubbs II catalyst (7 mg) was added
  3. concentrationThe mixture was concentrated to dryness
  4. custompurified by prep

Sources & evidence

ORD record
ord-4de7c34782bd476aa8aed69a69286c35
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937080B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes