Hydrochloric Acid → HCID 68733634, compound

HRID 529135Notes

Reaction equation

[CH3:1][C@H:2]1[C:10]2[C:9]([N:11]3[C:31]4[C:26](=[C:27]([CH2:32][NH:33][C:34]5[N:39]=[CH:38][CH:37]=[CH:36][N:35]=5)[CH:28]=[CH:29][CH:30]=4)[C:13]4([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)[CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1.[ClH:40]>>[ClH:40].[ClH:40].[CH3:1][C@H:2]1[C:10]2[C:9]([N:11]3[C:31]4[C:26](=[C:27]([CH2:32][NH:33][C:34]5[N:35]=[CH:36][CH:37]=[CH:38][N:39]=5)[CH:28]=[CH:29][CH:30]=4)[C:13]4([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]4)[CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68761423HCID 68761423, compound

Product 1

HCID 68733634HCID 68733634, compoundYield 99%

Procedure

A solution of (R)-tert-butyl 1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-4-((pyrimidin-2-ylamino)methyl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (4 mg, 7.58 μmol) and HCl (50.0 μL; 4N in dioxane) was stirred at ambient temperature overnight. The solvent was removed to yield (R)—N-((1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)pyrimidin-2-amine bishydrochloride as a solid (4.0 mg, 7.6 mmol, >99%). 1H NMR (400 MHz, CD3OD) δ 8.77 (s, 1H), 8.59 (br s, 2H), 7.99 (br d, J=6.6 Hz, 1H), 7.35 (t, J=8.2 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 6.98 (t, J=5.1 Hz, 1H), 4.95 (d, J=3.12 Hz, 2H), 4.69 (d, J=10.2 Hz, 1H), 4.26 (d, J=10.5 Hz, 1H), 3.96-3.91 (m, 1H), 3.74-3.71 (m, 1H), 3.64-3.58 (m, 4H), 3.60-3.52 (m, 2H), 3.46 (m, 2H), 3.14-3.10 (m, 2H), 2.95-2.85 (m, 1H), 2.65-2.55 (m, 2H), 1.92 (d, J=12.9 Hz, 1H), 1.95-1.88 (m, 2H), 1.27 (m, 6H), 1.13 (d, J=5.9 Hz, 1H). LCMS (APCI+) M+H+ 428 (100%); Rt=2.49 min. HPLC purity at 254 nm >99%, Rt=1.84 min.

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-a5898254aa1243bea4797efa47784089
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346805B2

Reaction notes

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