Sodium Hydroxide → HCID 67071512, compound

HRID 874330Notes

Reaction equation

C[O:2][C:3](=[O:34])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:30](=[CH:31][CH:32]=1)[O:29][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:33].[OH-].[Na+]>>[CH3:28][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH2:18][N:14]2[CH2:15][CH2:16][CH2:17][C:11]3([CH2:10][C:9](=[O:33])[C:8]4[C:30](=[CH:31][CH:32]=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:34])=[O:2])[CH:7]=4)[O:29]3)[CH2:12][CH2:13]2)=[CH:20]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 67071571HCID 67071571, compound

Product 1

HCID 67071512HCID 67071512, compound

Procedure

(±)-(E)-3-[1′-(1-Methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (350 mg, 0.76 mmol) was hydrolyzed with 1 M NaOH (0.99 ml) following the procedure described in Example 30, Step A, giving ((±)-(E)-3-[1′-(1-methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid as a white solid [LC-MS: (ES+) MH+: 445]. The obtained acid was suspended in DCM (15 ml), treated with TEA (0.16 ml, 1.14 mmol) and then with EDC (218 mg, 1.14 mmol), HOBt (154 mg, 1.14 mmol) and NH2OTHP (106 mg, 0.905 mmol) following the procedure described in Example 30, Step B, giving (±)-(E)-3-[1′(1-methyl-1H-indol-3-ylmethyl)-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (280 mg) as a light yellow solid.

Sources & evidence

ORD record: ord-142418c23b344102b6c40620e37a392f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980877B2

Reaction notes

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