tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate → HCID 66760943, compound

HRID 389569Notes

Reaction equation

HRID 389569 reaction equation
I[C:2]1[CH:7]=[N:6][C:5]([NH2:8])=[C:4]2[O:9][C:10]([C:12]3[C:20]4[C:15](=[CH:16][N:17]=[CH:18][CH:19]=4)[S:14][CH:13]=3)=[CH:11][C:3]=12.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[N:31][N:32]([CH:34]3[CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]3)[CH:33]=2)O1>>[NH:36]1[CH2:37][CH:34]([N:32]2[CH:33]=[C:29]([C:2]3[CH:7]=[N:6][C:5]([NH2:8])=[C:4]4[O:9][C:10]([C:12]5[C:20]6[C:15](=[CH:16][N:17]=[CH:18][CH:19]=6)[S:14][CH:13]=5)=[CH:11][C:3]=34)[CH:30]=[N:31]2)[CH2:35]1

Participants

3

Reactant 2

HCID 54576812tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylateHCID 66760274HCID 66760274, compound

Product 1

HCID 66760943HCID 66760943, compound

Procedure

The title compound was prepared from 4-iodo-2-thieno[2,3-c]pyridine-3-yl-furo[2,3-c]pyridine-7-ylamine and tert-butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate by a procedure analogous to Example 68 followed by deprotection by a procedure analogous to Example 64, Step B. 1H NMR (400 MHz, CD3OD): δ 9.29 (s, 1 H), 8.75 (s, 1 H), 8.63 (d, J=6.1 Hz, 1 H), 8.59 (d, J=6.1 Hz, 1 H), 8.26 (s, 1 H), 8.08 (s, 1H), 7.96 (s, 1H), 7.62 (s, 1H), 5.32 (m, 1H), 4.45 (m, 4H); MS (ESI): 389.18 [M+H]+; HPLC tR=0.25 min (HPLC: Analytical—2 min).

Workup

  1. customHPLC tR=0.25 min (HPLC: Analytical—2 min)

Sources & evidence

ORD record
ord-e7cb403151964aae9c7cee402b0c920e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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