2-(But-3-en-1-yloxy)-5-fluorobenzylamine → 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

HRID 1481975Notes

Reaction equation

[Na+].[CH2:2]([C:6]1([CH3:35])[CH2:11][CH2:10][N:9]([C:12]2[N:17]3[CH:18]=[C:19]([C:21]([O-:23])=O)[N:20]=[C:16]3[CH:15]=[C:14]([CH3:24])[C:13]=2[C@H:25]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:26]([O:28][CH3:29])=[O:27])[CH2:8][CH2:7]1)[CH2:3][CH:4]=[CH2:5].[CH2:36]([O:40][C:41]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:42]=1[CH2:43][NH2:44])[CH2:37][CH:38]=[CH2:39].C(OC1C=CC=CC=1CNC(C1N=C2C=C(C)C([C@H](OC(C)(C)C)C(OC)=O)=C(N3CCC(CCC=C)(C)CC3)N2C=1)=O)C=C>>[CH2:2]([C:6]1([CH3:35])[CH2:11][CH2:10][N:9]([C:12]2[N:17]3[CH:18]=[C:19]([C:21](=[O:23])[NH:44][CH2:43][C:42]4[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:41]=4[O:40][CH2:36][CH2:37][CH:38]=[CH2:39])[N:20]=[C:16]3[CH:15]=[C:14]([CH3:24])[C:13]=2[C@H:25]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[C:26]([O:28][CH3:29])=[O:27])[CH2:8][CH2:7]1)[CH2:3][CH:4]=[CH2:5]

Participants

Reactant 3

HCID 1076949852-(But-3-en-1-yloxy)-5-fluorobenzylamine

HCID 118308860(S)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid sodium salt

HCID 118308904(S)-methyl 2-(2-((2-(allyloxy)benzyl)carbamoyl)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

Product 1

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)acetateYield 75%

Procedure

Prepared from (S)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylic acid sodium salt and 2-(but-3-en-1-yloxy)-5-fluorobenzylamine in 75% yield using the same procedure as (S)-methyl 2-(2-((2-(allyloxy)benzyl)carbamoyl)-5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. 1H NMR (500 MHz, CDCl3) [note: appears to be 2:1 mixture of rotamers, major rotamer transcribed] δ 8.24-8.21 (m, 1H), 7.90-7.81 (m, 1H), 7.23-7.18 (m, 1H), 7.14-7.09 (m, 1H), 6.95-6.87 (m, 1H), 6.83-6.77 (m, 1H), 6.12-6.08 (m, 1H), 6.05-5.89 (m, 2H), 5.28-5.21 (m, 1H), 5.19-5.15 (m, 1H), 5.14-4.98 (m, 2H), 4.69-4.64 (m, 2H), 4.07 (s, 2H), 3.74-3.73 (m, 1H), 3.71 (s, 3H), 3.64-3.49 (m, 1H), 3.14-2.93 (m, 1H), 2.91-2.83 (m, 1H), 2.70-2.60 (m, 2H), 2.47-2.46 (m, 3H), 2.17-2.09 (m, 2H), 1.71-1.60 (m, 6H), 1.26 (s, 9H), 1.15 (s, 3H); LCMS (ESI, M+1): 649.35.

Sources & evidence

ORD record: ord-050b37798d0b4826bf0700230190ab3c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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