Hydrazine hydrate (1:1) → HCID 69812780, compound

HRID 529084Notes

Reaction equation

O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:22]3([CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)[CH2:21][N:20]([C:35]3[C:36]4[C@H:43]([CH3:44])[CH2:42][CH2:41][C:37]=4[N:38]=[CH:39][N:40]=3)[C:17]2=[CH:18][CH:19]=1.O.NN>CCO>[NH2:3][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:22]3([CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH2:24][CH2:23]3)[CH2:21][N:20]([C:35]3[C:36]4[C@H:43]([CH3:44])[CH2:42][CH2:41][C:37]=4[N:38]=[CH:39][N:40]=3)[C:17]2=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (R)-tert-butyl 5-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.014 g, 0.023 mmol) in EtOH (0.2 mL) was added hydrazine monohydrate (0.012 ml, 0.26 mmol). The solution was heated at 40° C. for 4 hours. After cooling, the solid was filtered and rinsed with EtOH. The filtrate was concentrated to dryness. The crude product was purified by column chromatography (10% MeOH/DCM then 10% MeOH/DCM+ 1% NH4OH) to yield (R)-tert-butyl 5-(2-aminoethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.009 g, 82%). LCMS (APCI+) m/z 464 [M+H]+; Rt=3.22 min.

Workup

temperatureAfter cooling
filtrationthe solid was filtered
washrinsed with EtOH
concentrationThe filtrate was concentrated to dryness
customThe crude product was purified by column chromatography (10% MeOH/DCM

Sources & evidence

ORD record: ord-3d0de29228874b8bbb319841b23a8540
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346805B2

Reaction notes

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