Acetonitrile → HCID 66662062, compound

HRID 557912Notes

Reaction equation

CN1CCOCC1.[N:8]1([C:14]2[N:19]=[CH:18][C:17]([C:20]3([C:23]([N:25]4[CH2:29][CH2:28][C@@:27]5([C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=6[C:31](=[O:38])[O:30]5)[CH2:26]4)=[O:24])[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH:39]1([C:42](O)=[O:43])[CH2:41][CH2:40]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(#N)C>>[CH:39]1([C:42]([N:11]2[CH2:12][CH2:13][N:8]([C:14]3[N:19]=[CH:18][C:17]([C:20]4([C:23]([N:25]5[CH2:29][CH2:28][C@@:27]6([C:33]7[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=7[C:31](=[O:38])[O:30]6)[CH2:26]5)=[O:24])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH2:9][CH2:10]2)=[O:43])[CH2:41][CH2:40]1

Participants

Reactant 5

HCID 6342Acetonitrile

HCID 79724-Methylmorpholine

HCID 15655Cyclopropanecarboxylic acid

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

HCID 66661586HCID 66661586, compound

Product 1

HCID 66662062HCID 66662062, compound

Procedure

4-Methylmorpholine (2.0×10−1 μL, 0.00018 mol) was added to a mixture of (1R)-1′-{[1-(6-piperazin-1-ylpyridin-3-yl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (15 mg, 0.000036 mol, this compound was prepared in a way similar to that described in example 163), cyclopropanecarboxylic acid (3.4 μL, 0.000043 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (19 mg, 0.000043 mol) in acetonitrile (0.7 mL, 0.01 mol). The reaction mixture was stirred at room temperature overnight. The crude product was purified by prep-LCMS. LC/MS: 487.3 (M+H+).

Workup

customthis compound was prepared in a way similar to
customThe crude product was purified by prep-LCMS

Sources & evidence

ORD record: ord-3b298172e1144f0097e03fd463733829
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058288B2

Reaction notes

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