Azide → HCID 90924656, compound

HRID 251736Notes

Reaction equation

[N:1]([CH:4]([C:17]1[S:21][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:19][CH:18]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:15][CH3:16])[O:14][CH2:13][CH2:12][O:11]1)=[N+]=[N-].[N-]=[N+]=[N-]>>[CH2:15]([C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([NH2:1])[C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:19][CH:18]=2)[O:11][CH2:12][CH2:13][O:14]1)[CH3:16]

Participants

Reactant 2

HCID 33558Azide

HCID 91518795HCID 91518795, compound

Product 1

HCID 90924656HCID 90924656, compound

Procedure

5-[1-azido-6-(2-ethyl-1,3-dioxolan-2-yl)hexyl]-2-phenyl-1,3-thiazole from alcohol (N2) was prepared according to the procedure used in Example 89 Step 2. 1H NMR (300 MHz, CDCl3) δ: 8.00-7.90 (2H, d, J=7.5 Hz), 7.57 (1H, s), 7.45-7.35 (3H, m), 5.10 (1H, t, J=7.3 Hz), 3.95 (4H, s), 1.89-1.78 (2H, m), 1.65-1.55 (4H, m), 1.45-1.25 (6H, m), 0.90-0.80 (3H, m). MS (ES) C20H26N4O2S requires: 386, found: 387 (M+H)+. The azide was then reduced according to the Example 89 Step 3 to afford the desired amine (N3). 1H NMR (300 MHz, CDCl3) δ: 7.95 (2H, d, J=7.5 Hz), 7.57 (1H, s), 7.45-7.35 (3H, m), 4.95 (1H, t, J=7.3 Hz), 3.95 (4H, s), 1.89-1.78 (2H, m), 1.65-1.55 (4H, m), 1.45-1.25 (6H, m), 0.90-0.80 (3H, m). MS (ES) C20H28N2O2S requires: 360, found: 361 (M+H)+.

Sources & evidence

ORD record: ord-de98175cebb14553a74d2aca86eabcfb
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863294B2

Reaction notes

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