Formaldehyde → HCID 68764934, compound

HRID 529117Notes

Reaction equation

Cl.Cl.Cl[C:4]1[CH:5]=[C:6]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:11][N:10]([C:18]3[C:19]4[C@H:26]([CH3:27])[CH2:25][C@@H:24](O)[C:20]=4[N:21]=[CH:22][N:23]=3)[C:7]2=[CH:8][CH:9]=1.C=O>>[CH2:12]([N:15]1[CH2:16][CH2:17][C:12]2([C:6]3[C:7](=[CH:8][CH:9]=[CH:4][C:5]=3[CH2:22][NH:21][CH:20]([CH3:24])[CH3:19])[N:10]([C:18]3[C:19]4[C@H:26]([CH3:27])[CH2:25][CH2:24][C:20]=4[N:21]=[CH:22][N:23]=3)[CH2:11]2)[CH2:13][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:4][CH:5]=1

Participants

Reactant 2

HCID 712Formaldehyde

HCID 69810675HCID 69810675, compound

Product 1

HCID 68764934HCID 68764934, compoundYield 60%

Procedure

(R)—N-((1′-benzyl-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)propan-2-amine (33 mg, 60%) was prepared by the procedures described in Example 18, substituting (R)-(1′-benzyl-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methanamine trihydrochloride trihydrochloride for (5R,7R)-4-(5-chlorospiro[indoline-3,4′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride, and substituting acetone for formaldehyde. LCMS (APCI+) m/z 482 [M+H]+; Rt=2.59 min.

Sources & evidence

ORD record: ord-8d1f7cf3b3fe4d01866294cecabab1bb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346805B2

Reaction notes

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