Hydrochloric Acid → HCID 67045030, compound

HRID 875675Notes

Reaction equation

HRID 875675 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH:21]3[CH2:23][CH2:22]3)=[CH:19][N:18]=[C:17]3[N:24](C(OC(C)(C)C)=O)[CH:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)[C:16]=23)[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:50]>CCOCC>[ClH:50].[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH:21]3[CH2:22][CH2:23]3)=[CH:19][N:18]=[C:17]3[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)[C:16]=23)[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 67045362HCID 67045362, compound

Product 1

HCID 67045030HCID 67045030, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-tert-Butyl 4-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-5-cyclopropyl-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (81 mg, 0.14 mmol) was treated with TFA followed by 2M HCl in ether as described in Example 1, Step K, to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide hydrochloride (33 mg, 48% yield). 1H NMR (400 MHz, D2O) δ 9.16 (d, 1H), 8.82 (dd, 1H), 8.72 (dt, 1H), 7.95 (s, 1H), 7.92 (dd, 1H), 7.41 (s, 1H), 3.98-3.93 (m, 1H), 3.61-3.53 (m, 1H), 3.32-3.25 (m, 2H), 3.15-3.06 (m, 1H), 1.96-1.85 (m, 2H), 1.64-1.56 (m, 1H), 1.52-1.41 (m, 1H), 1.39-1.27 (m, 1H), 0.98-0.92 (m, 2H), 0.70-0.61 (m, 2H); LCMS (APCI+) m/z 377.2 (M+H)+, Retention time=2.12 minutes (Method 2).

Sources & evidence

ORD record
ord-a957e86066e64142a3918957dd7cba89
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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