HCID 69812225, compound → HCID 44197605, compound

HRID 529148Notes

Reaction equation

C([Mg]Br)C.Cl.Cl.Cl.[CH:8]1([C@H:13]2[C:21]3[C:20]([N:22]4[C:35]5[C:30](=[C:31]([CH2:36][NH:37][CH:38]([CH3:40])[CH3:39])[CH:32]=[CH:33][CH:34]=5)[C:24]5([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH2:23]4)=[N:19][CH:18]=[N:17][C:16]=3[CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([C@H:13]2[C:21]3[C:20]([N:22]4[C:35]5[C:30](=[C:31]([CH2:36][NH:37][CH:38]([CH3:40])[CH3:39])[CH:32]=[CH:33][CH:34]=5)[C:24]5([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH2:23]4)=[N:19][CH:18]=[N:17][C:16]=3[CH2:15][CH2:14]2)[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

Reactant 2

HCID 69812225HCID 69812225, compound

HCID 178418443HCID 178418443, compound

Product 1

HCID 44197605HCID 44197605, compound

Procedure

(S)—N-((1-(5-Cyclopentyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)propan-2-amine was prepared as described in Example 80, substituting cyclopentylmagnesium bromide for ethylmagnesium bromide in Step 1. 1H NMR (CDCl3, 400 MHz) δ 8.62 (s, 1H), 7.08-7.26 (m, 2H), 6.97 (d, 1H), 4.01 (s, 2H), 3.88-3.97 (m, 2H), 3.42 (m, 1H), 3.14 (dd, 2H), 2.96-2.98 (m, 3H), 2.80 (dt, 2H), 2.57-2.59 (m, 1H), 2.09-2.21 (m, 3H), 1.93 (m, 1H), 1.86 (m, 2H), 1.59 (d, 1H), 1.34-1.48 (m, 6H), 1.11 (s, 6H), 0.99 (m, 1H). (S)—N-((1-(5-cyclopentyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)propan-2-amine trihydrochloride. MS (APCI+) [M+H]: 446.3.

Sources & evidence

ORD record: ord-c3552fe38f2f488cad5fef9c31508b8e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346805B2

Reaction notes

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