Hydrochloric Acid → HCID 68298700, compound

HRID 2271683Notes

Reaction equation

HRID 2271683 reaction equation
[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]4[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29]C(=O)OC(C)(C)C)[CH2:24]4)=[N:21][CH:22]=2)=[CH:13][C:12]([C:37]2[CH:42]=[C:41]([Cl:43])[C:40]([OH:44])=[C:39]([Cl:45])[CH:38]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.Cl>C(OCC)(=O)C>[ClH:43].[NH2:29][C@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:20]2[N:21]=[CH:22][C:17]([NH:16][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[C:12]([C:37]5[CH:38]=[C:39]([Cl:45])[C:40]([OH:44])=[C:41]([Cl:43])[CH:42]=5)[CH:13]=4)[N:8]=[CH:7][C:6]=3[C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[CH:18][CH:19]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86692898HCID 86692898, compound

Product 1

HCID 68298700HCID 68298700, compoundYield 182.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

(S)-tert-Butyl 1-(5-(3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate (5.7 g, 8.8 mmol) was reacted HCl (100 mL, 1.25M in methanol). The mixture was heated to 40° C. for 16 h. The reaction was diluted with ethyl acetate (100 mL). The resultant solid was filtered and washed with ethyl acetate. The solids were dissolved in a mixture of water, methanol, and acetonitrile. The solution was concentrated by lyophilization to obtain desired product (4.7 g, 81%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.36 (s, 1H), 8.32-8.22 (m, 3H), 8.08 (d, J=9.2 Hz, 1H), 7.90 (dd, J=9.5, 2.6 Hz, 1H), 7.48 (s, 2H), 7.36 (d, J=9.5 Hz, 1H), 4.51-4.45 (m, 1H), 4.11-4.03 (m, 1H), 3.53-3.36 (m, 3H), 2.87-2.78 (m, 1H), 2.27-2.20 (m, 1H), 2.06-1.97 (m, 1H), 1.85-1.72 (m, 2H), 1.25-1.10 (m, 4H); ESI MS m/z 548 [C29H27Cl2N5O2+H]+; HPLC 98.8% (AUC), tR=9.51 min.

Workup

  1. filtrationThe resultant solid was filtered
  2. washwashed with ethyl acetate
  3. dissolutionThe solids were dissolved in a mixture of water, methanol, and acetonitrile
  4. concentrationThe solution was concentrated by lyophilization

Sources & evidence

ORD record
ord-0f657862cb834f03b5d1d7835def4bff
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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