Methyl(2S)-2-{5-[4-(but-3-en-1-yl)-4-methylpiperidin-1-yl]-2-({[2-(but-3-en-1-yloxy)-5-fluorophenyl]methyl}carbamoyl)-7-methylimidazo[1,2-a]pyridin-6-yl}-2-(tert-butoxy)acetate → (2S)-2-(tert-Butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19-oxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acid

HRID 1481976Notes

Reaction equation

HRID 1481976 reaction equation
[CH2:1]([C:5]1([CH3:47])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20](=[O:35])[NH:21][CH2:22][C:23]4[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=4[O:30][CH2:31][CH2:32][CH:33]=[CH2:34])[N:19]=[C:15]3[CH:14]=[C:13]([CH3:36])[C:12]=2[C@H:37]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[C:38]([O:40]C)=[O:39])[CH2:7][CH2:6]1)[CH2:2]C=C.C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(CCCCCOC2C=CC=CC=2CNC3=O)CC1)C(O)=O)(C)(C)C>>[C:43]([O:42][C@@H:37]([C:12]1[C:13]([CH3:36])=[CH:14][C:15]2=[N:19][C:18]3=[CH:17][N:16]2[C:11]=1[N:8]1[CH2:9][CH2:10][C:5]([CH3:47])([CH2:1][CH2:2][CH2:34][CH2:33][CH2:32][CH2:31][O:30][C:24]2[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=2[CH2:22][NH:21][C:20]3=[O:35])[CH2:6][CH2:7]1)[C:38]([OH:40])=[O:39])([CH3:45])([CH3:46])[CH3:44]

Participants

3

Reactant 2

HCID 118308835Methyl(2S)-2-{5-[4-(but-3-en-1-yl)-4-methylpiperidin-1-yl]-2-({[2-(but-3-en-1-yloxy)-5-fluorophenyl]methyl}carbamoyl)-7-methylimidazo[1,2-a]pyridin-6-yl}-2-(tert-butoxy)acetateHCID 118316260(2S)-2-(tert-Butoxy)-2-{4,25-dimethyl-10-oxo-19-oxa-1,7,11,30-tetraazapentacyclo[23.2.2.16,9.02,7.013,18]triaconta-2,4,6(30),8,13(18),14,16-heptaen-3-yl}acetic acid

Product 1

HCID 118316261(2S)-2-(tert-Butoxy)-2-{15-fluoro-4,26-dimethyl-10-oxo-19-oxa-1,7,11,31-tetraazapentacyclo[24.2.2.16,9.02,7.013,18]hentriaconta-2,4,6(31),8,13(18),14,16-heptaen-3-yl}acetic acidYield 12%

Procedure

Prepared from methyl(2S)-2-{5-[4-(but-3-en-1-yl)-4-methylpiperidin-1-yl]-2-({[2-(but-3-en-1-yloxy)-5-fluorophenyl]methyl}carbamoyl)-7-methylimidazo[1,2-a]pyridin-6-yl}-2-(tert-butoxy)acetate in 12% yield using the same procedure as (2S)-2-(tert-butoxy)-2-{4,25-dimethyl-10-oxo-19-oxa-1,7,11,30-tetraazapentacyclo[23.2.2.16,9.02,7.013,18]triaconta-2,4,6(30),8,13(18),14,16-heptaen-3-yl}acetic acid. 1H NMR (500 MHz, DMSO-d6) δ 8.90-8.81 (m, 1H), 8.21 (s, 1H), 7.27 (dd, J=8.9, 3.1 Hz, 1H), 7.22 (s, 1H), 7.10-7.03 (m, 1H), 6.95 (dd, J=9.0, 4.4 Hz, 1H), 5.91 (s, 1H), 4.30 (t, J=5.0 Hz, 2H), 4.05-3.95 (m, 2H), 3.79-3.71 (m, 2H), 3.01 (d, J=11.0 Hz, 1H), 2.62 (d, J=11.0 Hz, 1H), 2.37 (s, 3H), 1.82-1.33 (m, 14H), 1.17 (s, 9H), 0.96 (s, 3H); LCMS (ESI, M+1): 609.3.

Sources & evidence

ORD record
ord-d2091ccd09e84688b569779bbf0619ee
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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